Substituted pyridine herbicides

ABSTRACT

Compounds of formula (I), in which the substituents are as defined in claim 1 and the agrochemically tolerated salts M+ and all stereoisomers and tautomers of the compounds of formula (I) are suitable for use as herbicides.

This application is a continuation of International Application PCT/EP99/10326, filed Dec. 22, 1999, which is fully incorporated by reference herein.

The present invention relates to novel, herbicidally active pyridine ketones, to their preparation, to compositions comprising these compounds, and to their use for controlling weeds, especially in crops of useful plants, or for inhibiting plant growth.

Herbicidally active pyridine ketones are described, for example, in WO 97/46530. There have now been found novel pyridine ketones which have herbicidal and growth-inhibitory properties.

The present invention therefore relates to compounds of the formula I

in which

p is 0 or 1;

R₅ is C₁-C₆haloalkyl;

R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, viny which is substituted by C₁-C₂alkoxycarbonyl or phenyl, or is C₂-C₆alkynyl, C₂-C₆haloalkynyl, ethynyl which is substituted by trimethylsilyl, hydroxyl, C₁-C₂alkoxy, C₁-C₂alkoxycarbonyl or phenyl, or is C₃-C₆allenyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyl which is substituted by halogen, or is C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-C₁-C₄alkoxy, C₁-C₄alkoxy-C₁-C₄alkoxy, C₁-C₄alkylthio-C₁-C₄alkoxy, C₁-C₄alkylsulfinyl-C₁-C₄alkoxy, C₁-C₄alkylsulfonyl-C₁-C₄alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, benzyl-S(O)_(n1)—, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylaminosulfonyl, di-(C₁-C₆alkylamino)sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl-containing groups, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro or R₂ is OS(O)_(n2)—R₂₁, N(R₂₃)—S(O)_(n3)—R₂₂, cyano, carbamoyl, C₁-C₄alkoxycarbonyl, formyl, halogen, thiocyanato, amino, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄alkyl, cyano-C₁-C₄alkyl, C₁-C₆alkylcarbonyloxy-C₁-C₄alkyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkyl, C₁-C₄alkoxycarbonyloxy-C₁-C₄alkyl, C₁-C₄thiocyanato-C₁-C₄alkyl, benzoyloxy-C₁-C₄alkyl, C₂-C₆oxiranyl, C₁-C₄alkylamino-C₁-C₄alkyl, di-(C₁-C₄-alkyl)amino-C₁-C₄alkyl, C₁-C₁₂alkylthiocarbonyl-C₁-C₄alkyl or for formyl-C₁-C₄alkyl, or R₂ is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C₁-C₄alkylene, —CH═CH—, —C≡C—, —CH₂O—, —CH₂N(C₁-C₄alkyl)—, —CH₂SO—, or —CH₂SO₂ group and it not being possible for each ring system to contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen;

R₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylaminosulfonyl, C₂-C₆dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or R₃ is —N(R₂₃)—S(O)_(n)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkyl-S(O)_(n)—C₁-C₄alkyl;

R₄ is hydrogen, C₁-C₆alkyl, hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkylsulfonyloxy, tosyloxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₁-C₄dialkylamino, C₁-C₄alkoxycarbonyl, C₁-C₄haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

or R₄ is a five to ten-membered monocyclic or R₃-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system, unless fused, being bonded to the pyridine ring directly or via a C₁-C₄alkylene, —CH═CH—, —C≡C—, —CH₂O—, —CH₂N(C₁-C₄alkyl)—, —CH₂S—, —CH₂SO—, or —CH₂SO₂— group and it not being possible for the ring system to contain more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₄alkoxy-C₁-C₂alkylthio, C₁-C₄alkylcarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂alkylthio, cyano-C₁-C₄alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen;

R₂₁ is C₁-C₄alkyl or C₁-C₄haloalkyl;

R₂₂ is C₁-C₄alkyl, C₁-C₄haloalkyl or di-(C₁-C₄alkyl)amino;

R₂₃, R₂₄, R₂₅ independently of one another are hydrogen or C₁-C₄alkyl;

n, n₁, n₂, n₃ and n₄ independently of one another are 0, 1 or 2;

Q is Q₁

 in which

R₆, R₇, R₆ and R₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkyl-S(O)_(n17), C₁-C₆alkyl-NHS(O)₂, C₁-C₆alkylamino, di-(C₁-C₆alkyl)amino, hydroxyl, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, hydroxy-C₁-C₆alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₆alkyl, tosyloxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkyl-S(O)_(n4)—C₁-C₆alkyl, cyano-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxy, benzyloxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyl-C₁-C₆alkyl, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl, thiocyanato-C₁-C₆alkyl, oxiranyl, C₁-C₆alkylamino-C₁-C₆alkyl, di(C₁-C₆alkyl)amino-C₁-C₆alkyl, formyl-C₁-C₆alkyl, C₁-C₆alkyloximo, halogen, cyano, nitro, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n18), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n5), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n19)N(C₁-C₄alkyl)₂, halogen, nitro, COOH or cyano;

or adjacent R₆ and R₇ or R₈ and R₉ together are —(CH₂)_(m)—, C(O)O(CH₂)_(n20)— or —S(O)_(n21)(CH₂)_(n22)—;

n₅, n₁₇, n₁₈, n₁₉ and n₂₁ independently of one another are 0, 1 or 2;

n₂₀ is 2 or 3;

n₂₂ is 2, 3 or 4;

m is 2, 3, 4, 5, or 6;

W is oxygen, S(O)_(n6), —CR₁₁R₁₂, —CR₆₃R₆₄CR₆₅R₆₆, —C(O)— or —NR₁₃;

R₆₃, R₆₄, R₆₅ and R₆₆ independently of one another are hydrogen or C₁-C₆alkyl, or R₆₅ together with R₇ or R₉ forms a direct bond;

n₆ is 0, 1 or 2;

R₁₁ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkylthio-C₁-C₄alkyl, C₁-C₄alkylthio-C₃-C₆cycloalkyl, C₁-C₄alkycarbonyloxy-C₁-C₄alkyl, C₁-C₄alkysulfonyloxy-C₁-C₄alkyl, tosyloxy-C₁-C₄alkyl, di-(C₁-C₃alkoxyalkyl)methyl, di-(C₁-C₃alkthioalkyl)methyl, (C₁-C₃alkoxyalkyl)-(C₁-C₃alkthioalkyl)methyl, C₃-C₅oxacycloalkyl, C₃-C₅thiacycloalkyl, C₃-C₄dioxacycloalkyl, C₃-C₄dithiacycloalkyl, C₃-C₄oxathiacycloalkyl, formyl, C₁-C₄alkoxycarbonyl, carbamoyl, C₁-C₄alkylaminocarbonyl, di-(C₁-C₄alkyl)aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n21), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n7), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n20)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano;

n₇, n₂₀ and n₂₁ independently of one another are 0, 1 or 2;

or R₁₂ together with R₆ or R₉ is a group —(CH₂)_(o)—;

o is 1, 2, 3, 4 or 5;

R₁₂ is hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl;

or R₁₂ together with R₁₁ is a group —(CH₂)_(m1);

m₁ is 2, 3, 4, 5, or 6;

R₁₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₂-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₁₄R₁₅N, R₁₄R₁₅NNH, R₁₆R₁₇NC(O)O—, R₁₆R₁₇NC(O)NH—, C₁-C₁₂alkyl-S(O)₂NR₁₈, C₁-C₄haloalkyl-S(O)₂NR₁₉, C₁-C₁₂alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, it being possible for the alkyl group to be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, or is C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)-NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)-NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano;

or R₁₀ is a group Ar₁-thio, Ar₂-sulfinyl, Ar₃-sulfonyl, —OCO-Ar₄ or NH-Ar₅ in which Ar₁, Ar₃, Ar₄ and Ar₅ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, and it being possible for each ring system to contain not more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen;

R₁₄, R₁₅, R₁₆, R₁₇ and R₁₈ independently of one another are hydrogen or C₁-C₆alkyl;

n₈, n₉, n₁₀, n₁₁, n₁₂, n₁₃ and n₁₄ independently of one another are 0, 1 or 2;

R₁₃ is hydrogen, C₁-C₄alkyl, C₁-C₄alkythio-C₁-C₄carbonyl, G₁-C₄alkylsulfinyl-C₁-C₄carbonyl, C₁-C₄alkylsulfonyl-C₁-C₄carbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylcarbonyl, phenylcarbonyl, or is phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄-alkylamino, C₁-C₄alkyl-S(O)_(n15), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n16), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, or cyano; and n₁₅ and n₁₆ independently of one another are 0, 1 or 2;

and the agrochemically tolerated salts M⁺ and all stereoisomers and tautomers of the compounds of the formula I.

The alkyl groups in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the abovementioned alkyl radicals. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

An alkylene group for example, —(CH₂)_(m)—, —(CH₂)_(m1)— or —(CH₂)_(o)— can be substituted by one or more methyl group; preferably, such alkylene groups are in each case unsubstituted. The same also applies to the —C(O)O(CH₂)_(n20)— and —S(O)_(n21)(CH₂)_(n22)— group and to all C₃-C₆-cycloalkyl-, C₃-C₅oxacycloalkyl-, C₃-C₅thiacycloalkyl-, C₃-C₄dioxacycloalkyl-, C₃-C₄-dithiacycloalkyl-, C₃-C₄oxathiacycloalkyl-containing groups.

Halogen is, as a rule, fluorine, chlorine, bromine or iodine. This also applies analogously to halogen in conjunction with other meanings such as haloalkyl or halophenyl.

Haloalkyl groups with a chain length of 1 up to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-fluoroprop-2-yl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl; haloalkyl groups in the meanings R₂, R₃ and, in particular, R₅ are preferably trichloromethyl, fluoromethyl, dichlorofluoromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoro-n-propyl.

Suitable as haloalkyl are monohalogenated or polyhalogenated alkenyl groups, where halogen is fluorine, chlorine, bromine and iodine, and in particular fluorine and chlorine, for example 1-chlorovinyl, 2-chlorovinyl, 2,2-difluorovinyl, 2,2-difluoroprop-1-en-2-yl, 2,2-dichlorovinyl, 3-fluoroprop-1-enyl, chloroprop-1-en-1-yl, 3-bromoprop-1-en-1-yl, 2,3,3-trifluoroprop-2-en-1-yl, 2,3,3-trichloroprop-2-en-1-yl and 4,4,4-trifluorobut-2-en-1-yl. Preferred amongst the monohalogenated, dihalogenated or trihalogenated C₂-C₆alkenyl groups are those which have a chain length of 2 to 5 carbon atoms.

Suitable as haloalkynyl are, for example, monohalogenated or polyhalogenated alkynyl groups, where halogen is bromine, iodine and, in particular, fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluorobut-2-yn-1-yl. Preferred amongst the monohalogenated or polyhalogenated alkynyl groups are those which have a chain length of 2 to 5 carbon atoms.

A monohalogenated or polyhalogenated C₃-C₆cycloalkyl group is, for example, the 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2,3,3-tetrafluorocyclobutyl or 2,2-difluoro-3,3-dichlorocyclobutyl group.

Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy and the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl, ethoxycarbonyl or tert-butoxycarbonyl. Haloalkoxy groups preferably have a chain length of 1 to 6 carbon atoms.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoroethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably fluoromethoxy, difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.

Alkylthio groups preferably have a chain length of 1 to 8 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.

Alkylamino is, for example, methylamino, ethylamino, n-propylamino, iso-propylamino or the butylamino isomers. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, di-butylamino and di-iso-propylamino. Preferred are alkylamino groups having a chain length of 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, iso-propoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have 1 to 6 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, iso-propylthiomethyl, iso-propylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl.

Phenyl, also as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl or tosyl can be in monosubstituted or polysubstituted form. In this case, the substituents can be in any of the ortho, meta and/or para position(s).

Allenyl is, for example, CH₂═C═CH₂ CH₂═CH—CH₂—CH═CH₂, CH₂═CH—CH₂—CH₂—CH═CH₂ or CH₂═CH—CH₂—CH═CH—CH₃.

The invention also extends to the salts M⁺ which the compounds of the formula 1, in particular those compounds of the formula I in which R₁₀ is O⁻M⁺, can form, preferably with amines, alkali metal bases, alkaline earth metal bases or quaternary ammonium bases The following must be emphasized as salt formers amongst the alkali metal bases and alkaline earth metal bases: the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium. Examples of amines which are suitable for ammonium salt formation are not only ammonia, but also primary, secondary and tertiary C₁-C₁₈alkylamines, C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso-propylamine, the four butylamine isomers, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methyinonylamine, methyl-pentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines for example, pyridine, quinoline, iso-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines for example anilines, methoxyanilines, ethoxyanilines, o-, m-, p-toluidines, phenylenediamines, naphthylamines and o-, m- and p-chloroanilines; but in particular triethylamine, iso-propylamine and di-iso-propylamine. Examples of quaternary ammonium bases which are suitable for salt formation are, for example, [N(R_(a) R_(b) R_(c) R_(d))]⁺OH⁻, where R_(a), R_(b), R_(c) and R_(d) independently of one another are C₁-C₄alkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions. M⁺ preferably represents an ammonium salt, in particular NH₄ ⁺, or an alkali metal, in particular potassium or sodium.

The compounds of the formula I can occur in various tautomeric forms, for example, if R₁₀ is hydroxyl, in the preferred formulation I′ and I′″

Preferred among the compounds of the formula I are those in which

p is 0;

R₅ is C₁-C₆haloalkyl;

R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, benzyl-S(O)_(n1)—, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆-alkylaminosulfonyl, C₂-C₆-dialkylaminosulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by C₁-C₃-alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or is OS(O)_(n2)—R₂₁, N(R₂₃)—S(O)_(n3)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄alkyl, cyano-C₁-C₄alkyl or C₁-C₄alkoxy-C₁-C₄alkoxy;

R₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylithio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylaminosulfonyl, C₂-C₆-dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or is —N(R₂₃)—S(O)_(n)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkyl-S(O)_(n)—C₁-C₄alkyl;

R₄ is hydrogen, C₁-C₆alkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyloxy, alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

or R₄ is a five- to ten-membered monocyclic or R₃-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C₁-C₄alkylene group and it not being possible for the ring system to contain more than 2 oxygen atoms and not more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆-Alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₄-alkoxy-C₁-C₂alkylthio, C₁-C₄alkylcarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂alkylthio, cyano-C₁-C₄alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen;

R₂₁ and R₂₂ independently of one another are C₁-C₄alkyl or C₁-C₄haloalkyl;

R₂₃, R₂₄ and R₂₅ independently of one another are hydrogen or C₁-C₄alkyl;

n, n₁, n₂, n₃ and n₄ independently of one another are 0, 1 or 2;

Q is Q₁

 in which

R₆, R₇, R₈ and R₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkyl-S(O)_(n17), C₁-C₆alkyl-NHS(O)₂, C₁-C₆alkylamino, di-(C₁-C₆alkyl)amino, hydroxyl, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆-alkynyloxy, hydroxy-C₁-C₆alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₆alkyl, tosyloxy-C₁-C₆alkyl, halogen, cyano, nitro, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄-alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n18), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n5), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n19)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano;

or adjacent R₆ and R₇ or R₈ and R₉ together are —(CH₂)_(m)—;

n₅ n₁₇, n₁₈ and n₁₉ independently of one another are 0, 1 or 2;

m is 2, 3, 4, 5, or 6;

W is oxygen, S(O)_(n6), —CR₁₁, R₁₂—, —C(O)— or —NR₁₃—;

n₆ is 0, 1 or 2;

R₁₁ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkylthio-C₁-C₄alkyl, C₁-C₄alkylcarbonyloxy-C₁-C₄alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₄alkyl, tosyloxy-C₁-C₄alkyl, di-(C₁-C₃alkoxyalkyl)methyl, di-(C₁-C₃alkylthioalkyl)methyl, (C₁-C₃alkoxyalkyl)-(C₁-C₃alkylthioalkyl)methyl, C₃-C₅oxacycloalkyl, C₃-C₅thiacycloalkyl, C₃-C₄dioxacycloalkyl, C₃-C₄-dithiacycloalkyl, C₃-C₄oxathiacycloalkyl, formyl, C₁-C₄alkoxycarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n21), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₇, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n20)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano;

n₇, n₂₀ and n₂₁ independently of one another are 0, 1 or 2;

or R₁₂ together with R₉ is a group —(CH₂)_(o)—;

o is 1, 2, 3, 4 or 5;

R₁₂ is hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl; or R₁₂ together with R₁₁ is a group —(CH₂)_(m1);

m₁ is 2, 3, 4, 5, or 6;

R₁₀ is hydroxyl, O⁻M⁺, halogen, C₁-C₁₂alkoxy, C₁-C₁₂alkylcarbonyloxy, C₂-C₄-alkenylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂-alkylcarbonyloxy, R₂₃R₂₄N—C(O)O, C₁-C₁₂alkylS(O)_(n8)—, C₁-C₄haloalkyl-S(O)_(n9)—, C₂-C₁₂-alkenylS(O)_(n10)—, C₂-C₁₂haloalkenylS(O)_(n11)—, C₂-C₁₂alkynylS(O)_(n12)—; benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl group, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n13), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n14), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano, or is C₁-C₄alkyl-S(O)₂O, phenyl-S(O)₂O, phenyl-S(O)₂O, (C₁-₄alkoxy)₂P(O)O, C₁-C₄alkyl(C₁-C₄alkoxy)P(O)O, or H(C₁-C₄alkoxy)P(O)O;

n₈, n₉, n₁₀, n₁₁, n₁₂, n₁₃ and no independently of one another are 0, 1 or 2;

R₁₃ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxycarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n15), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n16), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano;

n₁₅ and n₁₆ independently of one another are 0, 1 or 2;

and the agrochemically tolerated salts M⁺ and all stereoisomers and tautomers of the compounds of the formula I.

In a preferred group of compounds of the formula I, R₁₀ is halogen, thiocyanato, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂-haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂-alkenylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂-haloalkenylsulfinyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₂alkylsulfonyl, C₁-C₈alkyl-S(O)₂NH, C₁-C₈haloalkyl-S(O)₂NH, C₁-C₈alkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, C₂-C₁₈alkenylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂-alkylthiocarbonyloxy, R₁₆R₁₇NC(O)O—, R₁₆R₁₇NC(S)O—, benzylthio, benzylsulfinyl, benzylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted as indicated in claim 1; or is a group Ar₁-thio, Ar₁-sulfinyl, Ar₁-sulfonyl in which Ar₁ is a five- or six-membered monocyclic ring system which can be aromatic or partially saturated and can contain 1 to 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and which, in turn, can be substituted as indicated in claim 1; or is thienylcarbonyloxy or furylcarbonyloxy, it being possible for these, in turn, to be substituted by methyl or halogen, or pyridylcarbonyloxy which, in turn, can be substituted as indicated in claim 1.

In preferred compounds of the formula I, furthermore, R₁₀ is hydroxyl or O⁻M⁺.

Other compounds of the formula I which must be emphasized are those in which W is oxygen, —CR₁₁R₁₂— or —C(O)—, where, in particular when W is —CR₁₁R₁₂—,

a) R₆ is hydrogen, methyl, ethyl, cyano, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or methoxy; and R₇, R₈, R₉, R₁₁ and R₁₂ independently of one another are hydrogen, C₁-C₄alkyl, C₁-C₃haloalkyl, C₂-C₃alkenyl or C₂-C₃alkynyl, or

b) adjacent R₆ and R₇ and/or R₈ and R₉ together are —(CH₂)_(m)—, —C(O)O(CH₂)₂- or S(O)_(n21)(CH₂)₃—; or

c) R₆ is hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or methoxy and R₁₂ together with R₉ is —(CH₂)_(o)—.

Furthermore, preferred groups of compounds of the formula I are those in which

W is oxygen and R₆, R₇, R₈ and R₉ independently of one another are hydrogen or C₁-C₃alkyl; or

W is —C(O)— and R₆, R₇, R₈ and R₉ independently of one another are C₁-C₃alkyl; or

R₂ is hydrogen and R₃ is methyl; or

R₂ is methyl, ethyl, n-propyl, i-propyl, vinyl, methoxymethyl, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl or cyanomethyl.

Other compounds of the formula I which must be emphasized are those in which R₄ is hydrogen or methyl or R₅ is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl or difluoromethyl.

In a further preferred group of compounds of the formula I, R₃ is hydrogen, R₂ is C₁-C₄alkyl, C₁-C₃haloalkyl, cyclopropyl, C₂-C₃alkenyl, C₂-C₃haloalkenyl, C₂-C₃alkynyl, allenyl, C₁-C₂-alkoxy-C₁-C₂alkyl, C₁-C₂alkylthio-C₁-C₂alkyl, cyano-C₁-C₂alkyl, C₁-C₂alkoxycarbonyl-C₁-C₂-alkyl, C₁-C₄alkylcarbonyloxy-C₁-C₂alkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl or cyano.

The compounds of the formula I in which Q is a group Q₁ can be prepared using processes which are known per se, for example those described in EP-A-0 353 187 and EP-A-0 316 491, for example either by

a) reacting a compound of the formula III

in which R₂, R₃, R₄ and R₅ have the meaning given under formula I and X is a leaving group, for example halogen or cyano, with a compound of the formula II

in which R₆, R₇, R₈, R₉ and W have the meaning given under formula I in the presence of a base and in an inert organic solvent to give the compound of the formula IV

and subsequently isomerizing the latter, for example in the presence of a base and a catalytic amount of dimethylaminopyridine (DMAP) or a cyanide source; or

b) reacting a compound of the formula XVI

in which R₂, R₃, R₄ and R₅ have the meaning given under formula I with compounds of the formula II

in which R₆, R₇, R₈, R₉ and W have the meaning given under formula I in an inert organic solvent in the presence of a base and a coupling agent to give the compound of the formula IV

and subsequently isomerizing the latter, for example as described under route a). The preparation of the compounds of the formula I is illustrated in greater detail in reaction scheme 1 below.

The compounds of the formula I with the group Q₁ in which R₁₀ is hydroxyl can preferably be prepared in accordance with this reaction scheme. The starting material for the preparation of the compounds of the formula I in which Q is the group Q₁ and R₁₀ is hydroxyl is, in accordance with reaction scheme 1, route a), the carboxylic acid derivatives of the formula III in which X is a leaving group for example halogen, for example iodine, bromine and, in particular chlorine N-oxyphthalimide or N,O-dimethylhydroxylamino or part of an activated ester, for example

(formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or

(formed from N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC) and the corresponding carboxylic acid). These are reacted with the dione derivatives of the formula II in an inert organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, and in the presence of a base, for example an alkylamine, preferably triethylamine, an aromatic amine, for example pyridine or 4-dimethylaminopyridine (DMAP) to give the isomeric enol ethers of the formula IV. This esterification is successfully carried out at temperatures from 0° C. to 110° C.

The isomerization of the ester derivatives of the formula IV to give the dione derivatives of the formula I (in which R₁₀ is OH) can be carried out, for example, in analogy to EP-A-0 353 187 or EP-A-0 316 491 in the presence of a base, for example an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a catalytic amount of a cyanide source, for example acetone cyanohydrin or potassium cyanide. Both reaction steps can be carried out in situ without isolation of the intermediates IV, in particular when using a cyanide compound of the formula III (X=cyano), or in the presence of a catalytic amount of acetone cyanohydrin or potassium cyanide.

In accordance with reaction scheme 1, route b), the desired diones of the formula I (in which R₁₀ is hydroxyl) can be obtained, for example, analogously to Chem. Lett. 1975, 1045 by esterifying the carboxylic acids of the formula XVI with the dione derivatives of the formula II in an inert solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrite, e.g. acetonitrile or an aromatic hydrocarbon, e.g. toluene, in the presence of a base, for example an alkylamine, e.g. triethylamine, and a coupling agent, for example 2-chloro-1-methylpyridinium iodide. Depending on the solvent used, this esterification is successfully carried out at temperatures from 0° C. to 110° C. and first yields, as described under route a), the isomeric ester of the formula IV which can be isomerized as described under route a), for example in the presence of a base and a catalytic amount of DMAP, or a cyanide source, to give the desired dione derivatives of the formula I (R₁₀=hydroxyl).

The activated carboxylic acid derivatives of the formula III in reaction scheme I (route a) in which X is a leaving group, for example halogen, e.g. bromine, iodine or, in particular, chlorine, can be prepared by known standard methods, for example as described by C. Ferri “Reaktionen der organischen Synthese” [“Reactions in organic synthesis”], Georg Thieme Verlag, Stuttgart, 1978, page 460 et seq. This is shown in the reaction scheme 2 which follows.

In accordance with reaction scheme 2, the compounds of the formula III in which X has the abovementioned meaning are prepared, for example, by using a halogenating agent, for example thionyl halides, e.g. thionyl chloride or thionyl bromide; phosphorus halides or phosphorus oxyhalides, e.g. phosphorus pentachloride or phosphorus oxychloride, or phosphorus pentabromide or phosphoryl bromide; or oxalyl halides, for example oxalyl chloride, or by employing a reagent for forming activated esters, for example N,N′-dicyclohexylcarbodiimide (DCC) or N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (EDC), of the formula XVII. Examples of meanings of X for the compound of the formula XVII as halogenating agent is a leaving group, for example halogen, e.g. fluorine, bromine or iodine and, in particular, chlorine, and W₁ is, for example, PCl₂, SOCl, SOBr or ClCOCO.

The reaction is preferably carried out in an inert organic solvent, for example in aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbons, e.g. n-hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chlorobenzene, at reaction temperatures in the range of −20° C. to the reflux temperature of the reaction mixture, preferably at 40-150° C., and in the presence of a catalytic amount of N,N-dimethylformamide. Such reactions are generally known, and various variations with regard to the leaving group X are described in the literature.

Compounds of the formula I in which R₁₀ is other than hydroxyl or halogen can be prepared by conversion methods which are generally known from the literature, for example by acylation or carbamoylation methods using appropriate acid chlorides in the presence of a suitable base, starting from compounds in which R₁₀ is hydroxyl, or can be prepared by nucleophilic substitution reactions on chlorides of the formula I in which R₁₀ is halogen, which can also be obtained by known methods by reaction with a chlorinating agent such as phosgene, thionyl chloride or oxalyl chloride. In this case, examples of compounds which are employed are suitably substituted amines, or, directly, hydroxylamines, or alkylsulfonamides, mercaptans, thiophenols, phenols, Ar₅—NH₂ or Ar₁—SH, in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.

Compounds of the formula I in which R₁₀ contains thio groups can be oxidized in analogy to known standard methods, for example using peracids, e.g. metachloroperbenzoic acid (m-CPBA) or peracetic acid, to give the corresponding sulfones and sulfoxides of the formula I. The degree of oxidation on the sulfur atom (SO— or SO₂—) can be controlled by the amount of oxidant.

Also, the resulting derivatives of the formula I in which R₁₀ is other than hydroxyl can exist in various isomeric forms which, if appropriate, can be isolated in pure form. The invention therefore also extends to all of these stereoisomeric forms. Examples of these isomeric forms are the formulae I*, I** and I*** below in which Q is the group Q₁ (see also note and scheme on page 10 above).

All other compounds from within the scope of the formula I can be readily prepared taking into consideration the chemical properties of the pyridyl or Q moiety.

The end products of the formula I can be isolated in the customary manner by concentration or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable eluent.

Furthermore, the skilled worker knows in which sequence certain reactions are expediently carried out to avoid any side reactions. Unless a directed synthesis for isolating pure isomers is carried out, the product may be obtained as a mixture of two or more isomers. The isomers can be resolved by methods known per se.

Compounds of the formula I in which n is 1, i.e. the corresponding N-oxides of the formula I, can be synthesized by reacting a compound of the formula I in which n is 0 with a suitable oxidant, for example with the H₂O₂-urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride.

Compounds of the formula I in which R in the ortho-position relative to the pyridine nitrogen is 1-chloro-C₁-C₂alkyl, 1-hydroxy-C₁-C₂alkyl, 1-(C₁-C₆alkylcarbonyloxy)-C₁-C₂alkyl, 1-benzoyloxy-C₁-C₂alkyl, 1-(C₁-C₄alkoxycarbonyloxy)-C₁-C₂alkyl, 1-(C₁-C₄alkylthio)-C₁-C₂-alkyl, 1-(C₁-C₄alkylsulfinyl)-C₁-C₂alkyl, 1-(C₁-C₄alkylsulfonyl)-C₁-C₂alkyl, 1-thiocyanato-C₁-C₂alkyl, 1-cyano-C₁-C₂alkyl, can also be prepared by, for example, heating an N-oxide of the formula I under known reaction conditions, for example in the presence of tosyl chloride (see, for example, Parham, W. E.; Sloan, K. B.; Reddy, K. R.; Olson, P. E.; J Org Chem 1973, 38, 927) or in the presence of an acid anhydride (see, for example, Konno, K.; Hashimoto, K.; Shirahama, H.; Matsumoto, T.; Heterocycles 1986, 24, 2169) and, if appropriate, subsequently further reacting the product. These reaction sequences may be demonstrated with reference to the following example:

Compounds of the formula I in which R in the ortho-position relative to the pyridine nitrogen, in particular 1-bromo-C₁-C₂alkyl, 1-chloro-C₁-C₂alkyl, 1-fluoro-C₁-C₂alkyl, 1,1-dibromomethyl, 1,1dichloromethyl, formyl, 1-(C₁-C₄alkylthio)-C₁-C₂alkyl, 1-(C₁-C₄alkylsulfinyl)-C₁-C₂alkyl, 1-(C₁-C₄alkylsulfonyl)-C₁-C₂alkyl, 1-thiocyanato-C₁-C₂alkyl or 1-cyano-C₁-C₂alkyl, can also be prepared, for example, by oxidizing a compound of the formula I in which R₁₀ is, in particular, chlorine, C₁-C₄alkoxycarbonyloxy or benzoylcarbonyloxy under known halogenation conditions, for example with N-bromosuccinimide or N-chlorosuccinimide in the presence of light and a free-radical initiator, for example benzoyl peroxide, to give the 1-bromo or 1-chloro, 1,1-dibromo or 1,1-dichloro compound, and subsequently refunctionalizing the latter to give the corresponding derivatives. Again, these reaction sequences may be demonstrated with reference to the example below.

Compounds of the formula I can also be synthesized by reacting a compound of the formula I in which p is 0 and R₂ is C₁-C₆alkyl with a suitable base, for example lithium diisopropylamide or n-butyllithium, at temperatures between −100 and −20° C. (preferably −70 and −50° C.) in an inert solvent (for example tetrahydrofuran) to give the corresponding dianion. The skilled worker knows how such carbanions can be converted by means of electrophilic substitution, for example with a chloroformic ester. This reaction sequence may be demonstrated with reference to the following example:

Other compounds from within the scope of the formula I can be prepared with suitable electrophiles taking into consideration the chemical properties of the pyridyl or Q moiety.

The compounds of the formula IIIa

in which

R₅₀₁ is C₁-C₆haloalkyl;

R₃₀₁ is hydrogen;

R₄₀₁ is hydrogen or C₁-C₆alkyl; and

R₂₀₁ is C₁-C₆alkyl, C₁-C₆haloalkyl-C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, or C₁-C₂-alkoxycarbonyl- or phenyl-substituted vinyl, C₂-C₆alkynyl or C₂-C₆haloalkynyl; or trimethylsilyl-, hydroxyl-, G₁-C₂alkoxy-, C₁-C₂alkoxycarbonyl- or phenyl-substituted ethynyl or C₃-C₆allenyl; or C₃-C₆cycloalkyl, halogen-substituted C₃-C₆cycloalkyl, C₁-C₄alkoxy-C₁-C₄-alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄alkyl, cyano-C₁-C₄alkyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkyl, C₁-C₄-thiocyanato, oxiranyl, C₁-C₄alkylamino-C₁-C₄alkyl, C₁-C₄dialkylamino-C₁-C₄alkyl, hydroxy-C₁-C₄alkyl, C₁-C₁₂alkylthiocarbonyl-C₁-C₄alkyl or formyl-C₁-C₄alkyl, or R₂₀₁ is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C₁-C₄-alkylene, —CH═CH—, —C≡C—, —CH₂O—, —CH₂N(C₁-C₄alkyl)—, —CH₂S—, —CH₂SO— or —CH₂SO₂— group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆-alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro, and where the substituents on the nitrogen in the heterocyclic ring are other than halogen; and X is halogen or cyano, are novel and were developed specifically for the preparation of the compounds of the formula I and are therefore a further subject of the present invention.

The compounds of the formula XVIa

in which R₂₀₁, R₃₀₁, R₄₀₁ and R₅₀₁ have the abovementioned meaning, with the proviso that, if R₅₀₁ is trifluoromethyl and, simultaneously, R₃₀₁ and R₄₀₁ are hydrogen, then R₂₀₁ is other than C₁-C₆alkyl, are novel and therefore a further subject of the present invention.

The compounds of the formula Q₁ (or formula II) are known and can be prepared by met hods similar to those described, for example in J. Org. Chem. (1977), 42, 1163-9, Brit. UK Pat. Appl. GB 2205316, DE 3902818, GB 8706557, DE 4434987, WO 9213821 and Aust. J. Chem. (1976), 29(11), 2525-31, Chem. Commun. (1998), (16), 1691-1692.

The compounds of the formula XVI (or XVIa and XVIb) are synthesized by methods similar to known methods, for example as in Heterocycles, 46, 129 (1997) or Helvetica Chimica Acta 71, 596 (1988), and is characterized in that either

a) a compound of the formula V

 in which R₃₀₁ is hydrogen;

R₄₀₁ is hydrogen, C₁-C₆alkyl or phenyl, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro;

or R₄₀₁ is a five- to ten-membered monocyclic or fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₄alkoxy-C₁,C₂alkylthio, C₁-C₄alkylcarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂-alkylthio, cyano-C₁-C₄alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; and

R₁₄ is C₁-C₄alkyl;

is acylated with a compound of the formula VI

in which R₅₀₁ is C₁-C₆haloalkyl to give the compound of the formula VII

in which R₃₀₁, R₄₀₁, R₅₀₁ and R₁₄ have the abovementioned meaning in the presence of a base, for example an aromatic amine, e.g. pyridine, and the alkoxy group is subsequently exchanged for the amino group with ammonia in an organic solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile. The resulting compound of the formula VIII

is subsequently subjected to a condensation reaction with a compound of the formula IX

in which R₂₀₁ is C₁-C₆alkyl, C₁-C₆haloalkyl-C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆-alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄-alkyl, cyano-C₁-C₄alkyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkyl, C₁-C₄alkoxycarbonyloxy-C₁-C₄alkyl, C₁-C₄thiocyanato-C₁-C₄alkyl, oxiranyl, C₁-C₄alkylamino-C₁-C₄alkyl, di-(C₁-C₄alkyl)amino-C₁-C₄alkyl or formyl-C₁-C₄alkyl;

or R₂₀₁ is a group Ar₆—C₁-C₄alkyl in which Ar₆ is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆-alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen, and R₁₄ has the abovementioned meaning, and subsequently hydrolysing the resulting compound of the formula Xa

is subsequently hydrolysed to give the compound of the formula XVIa

in which R₂₀₁, R₃₀₁, R₄₀₁ and R₅₀₁ have the abovementioned meaning; or

b) a compound of the formula XI

 in which R₁₄ has the abovementioned meaning is subjected to a condensation reaction with a compound of the formula XII

and the resulting compound of the formula XIII

in which R₃, R₄ and R₅ have the abovementioned meaning and R₁₄ is C₁-C₄alkyl, is chlorinated to give the compound of the formula XIV

in which R₃, R₄, R₅ and R₁₄ have the abovementioned meaning (for example using POCl₃), and this compound is subsequently reacted with a nucleophile of the formula XV in which Z is SH, OH or amino and R₁₅ is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆-alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkyl, phenyl or benzyl, it being possible for the phenyl group, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃-alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or is C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄-alkylthio-C₁-C₄alkyl, C₁-C₄alkylsulfinyl-C₁-C₄alkyl, C₁-C₄alkylsulfonyl-C₁-C₄alkyl, C₁-C₄-alkylsulfonyl or di-(C₁-C₄alkyl)aminosulfonyl, or R₁₅ is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆-haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆-haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, (CH₂)_(n)R₇, NR₈R₉, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and substituents on the nitrogen in the heterocyclic ring being other than halogen, in the presence of a base to give compounds of the formula Xb

in which R₁₄, R₁₅, R₃, R₄, R₅ and Z have the abovementioned meanings and the resulting compound is subsequently hydrolysed to give the compound of the formula XVIb

in which R₁₅, R₃, R₄, R₅ and Z have the abovementioned meaning.

Compounds in which Z-R₁₅ and Z are oxygen and R₁₅ is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆-alkynyl, C₁-C₆haloalkyl, C₃-C₆haloalkenyl, cyano-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkylthio-C₁-C₄alkyl or C₁-C₄alkoxycarbonyl-C₁-C₄alkyl can also be reacted starting from XIII by direct alkylation with the corresponding alkylating agent L-R₁₅ XVa in which L is a leaving group such as chlorine, bromine, iodine, mesyloxy or tosyloxy.

Compounds of the formula XVIb in which Z-R₁₅ is fluorine are prepared by reacting a compound of the formula XIV with potassium fluoride and, if appropriate, a catalytic amount of 18-crown-6 in the presence of a polar aprotic solvent, for example acetonitrile, dimethylformamide or sulfolane. Compounds of the formula XVIc in which Z-R₁₅ is hydrogen are prepared by reducing the chlorine group in formula XIV, for example with hydrogen in the presence of a suitable metal catalyst or with ammonium formate, in a suitable solvent. The preparation of the compounds of the formula XVI or XVIa, XVIb and XVIc are illustrated in greater detail in reaction schemes 3 and 4 which follow.

Compounds of the formula XVId in which R₂ is bromomethyl, cyanomethyl, thiocyanatomethyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, a C₁-C₂alkoxycarbonyl- or phenyl-substituted vinyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, a trimethylsilyl-, hydroxyl-, C₁-C₂alkoxy-, C₁-C₂alkoxycarbonyl- or phenyl-substituted ethynyl, C₃-C₆allenyl, C₃-C₆cycloalkyl or mono or polyhalogenated C₃-C₆cycloalkyl can be prepared, for example, in accordance with generally known conversion methods which are shown in reaction scheme 4a.

Intermediates of the formula XVIa in which R₅₀₁ is CF₂Cl are prepared as described in scheme 3 or by reacting a compound of the formula Xa in which R₅₀₁ is trichloromethyl with hydrofluoric acid in a pressurized vessel at temperatures between 0 and 220° C. (preferably 60-200° C.).

Compounds of the formula XVIa in which R₅₀₁ is CHF₂ can be prepared as in scheme 3 or by heating a compound of the formula Xa in which R₃₀₁, R₄₀₁, R₁₄ and R₂₀₁ have the abovementioned meaning and R₅₀₁ is CF₂Cl in an inert solvent, for example toluene or benzene, at temperatures between 25 and 120° C. (preferably 80-120° C.) with tributyltin hydride or 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane in the presence of a catalytic amount of azo-isobutyronitrile and subsequently hydrolysing the resulting compound to give the compound of the formula XVIa in which R₅₀₁ is CHF₂.

Compounds of the formula XVIa in which R₂₀₁, R₃₀₁, R₄₀₁ and R₅₀₁ have the abovementioned meaning can also be prepared by reacting a compound of the formula Xc in which R₁₄, R₃₀₁, R₄₀₁ and R₅₀₁ have the abovementioned meaning and R₂₀₁ is CH₂Cl by nucleophilic substitution, for example with an alkali metal iodide in an inert solvent, to give the corresponding iodides, or by means of gaseous hydrobromic acid in lower carboxylic acids such as glacial acetic acid to give the corresponding bromine derivatives (for example in accordance with US-3974166) or by means of alkali metal fluoride in a dipolar solvent such as sulfolane to give the corresponding fluorine derivatives, or, to prepare an alkoxy radical Xd, by reacting a halogen derivative Xc with an alcohol or phenol in the presence of a base such as sodium hydride or an alkaline earth metal oxide or alkaline earth metal carbonate or directly with an alkali metal alkoxide in an inert solvent such as dimethylformamide or in an excess of the alcohol ROH which corresponds to the group to be introduced at temperatures between −5 and 160° C., or, in order to prepare a corresponding aromatic or aliphatic thioether Xe, by reacting, analogously to what has been said above, either the halide Xc with an aliphatic or aromatic thiol in the presence of a base such as sodium hydride or with an alkali metal salt of a thiol in an inert solvent at −10-150° C., or, in order to prepare corresponding sulfinyl or sulfonyl derivatives Xe, by carrying out the reaction with an oxidant such as m-chloroperbenzoic acid or sodium periodate or sodium perborate, with the temperature control known in the art, depending on the degree of oxidation (for example −30° C.-+50° C. for n=1) or −20° C.-+100° C. for n=2) in an inert solvent such as dichloromethane to give Xf, or, in order to prepare cyanomethylene derivatives of the formula Xg, by reacting a halide of the formula Xc with an alkali metal cyanide or tetraalkylammonium cyanide or copper cyanide in an inert solvent such as dichloromethane, tetrahydrofuran or dimethylformamide at temperatures between 0° C. and 220° C.

The preparation of the compounds of the formula XVIa (R₅₀₁=CF₂Cl) and of the intermediates of the formulae Xc, Xd, Xe, Xf, and Xg are illustrated in greater detail in the reaction schemes 5, 6 and 7 which follow.

To prepare all other compounds of the formula X and XVI which are functionalized in accordance with the definition of R₂₀₁ (Z—R₁₅) to R₅₀₁, a multiplicity of known standard methods are suitable, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of the preparation methods which are suitable depending on the properties (reactivities) of the substituents in the intermediates.

The reactions to give compounds of the formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitrites such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone. The reaction temperatures are advantageously between −20° C. and +120° C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo-[5.4.0]undec-7-ene However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, may also be used as bases. The compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

All application methods which are conventionally used in agriculture, for example pre-emergence application, post-emergence application and seed treatment, as well as various methods and techniques, for example the controlled release of active ingredients, are suitable for the use according to the invention of the compounds of the formula I or of compositions comprising them. To this end, the active ingredient in solution is applied to mineral carriers for granules or to polymerized granules (urea/formaldehyde) and dried. If appropriate, an additional coating can be applied (coated granules), which allows the active ingredient to be released in a controlled manner over a specific period of time.

The compounds of the formula I can be employed as herbicides as such, i.e. as obtained from synthesis. However, they are preferably processed in the customary manner together with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. The application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the type of composition, are chosen to suit the intended aims and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or products which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients together with the formulation auxiliaries, for example solvents or solid carriers. Furthermore, surface-active compounds (surfactants) may additionally be used when preparing the formulations. Examples of solvents and solid carriers are indicated for example in WO 97/34485 on page 6.

Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, non-ionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties.

Examples of suitable anionic, non-ionic and cationic surfactants are enumerated, for example, in WO 97/34485 on pages 7 and 8.

The surfactants conventionally used in the art of formulation which are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” [“Surfactants Guide”], Carl Hanser Verlag, Munich/Vienna, 1981, and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81, are furthermore also suitable for preparing the herbicidal compositions according to the invention.

As a rule, the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions. The compositions can also comprise further additives such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.

As a rule, the active ingredients of the formula I are applied to the plant or its environment at rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the type of the action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and can, owing to these parameters, vary within wide limits.

The compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, rapeseed, maize and rice and for the non-selective control of weeds. Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicides by means of conventional plant breeding or by genetic engineering methods. The weeds to be controlled may be both mono- and dicotyledonous weeds such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

THE EXAMPLES WHICH FOLLOW ILLUSTRATE THE INVENTION IN GREATER DETAIL WITHOUT LIMITING IT. PREPARATION EXAMPLES Example H1 Preparation of 3-Hydroxy-4,4-dimethyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Compound A2-B24)

6.68 g (0.0305 mol) of methyl 2-methyl-6-trifluoromethylnicotinate (prepared as described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/water (3:1 mixture), and 1.92 g (0.046 mol) of lithium hydroxide hydrate are added portionwise at a temperature of 22° C. After 4 hours at 22° C., the reaction mixture is poured onto ethyl acetate and 2 N hydrochloric acid, and the organic phase is washed three times with water, dried with sodium sulfate and evaporated, and the residue is triturated with a small amount of hexane. After filtration, 5.69 g (90% of theory) of 2-methyl-6-trifluoromethylnicotinic acid of melting point 147-149° C. are obtained.

The resulting 2-methyl-6-trifluoromethylnicotinic acid (1.026 g, 0.005 mol) is dissolved in 20 ml of oxalyl chloride. Three drops of dimethylformamide are added and the mixture is refluxed for 1 hour. The mixture is then concentrated on a rotary evaporator and the residue (2-methyl-6-trifluoromethylnicotinoyl chloride) is taken up in 100 ml of methylene chloride. At a temperature of 0° C., 1.6 ml (0.0115 mol) of triethylamine and 0.7 g (0.005 mol) of 4,4-dimethylcyclohexane-1,3-dione are added. After 2 hours at a temperature of 22° C., the solvent is removed on a vacuum rotary evaporator, the residue which remains is dissolved in 55 ml of acetonitrile, and 0.15 ml (0.0016 mol) of acetone cyanohydrin and 0.79 ml (0.0057 mol) of triethylamine are added in order to subject the intermediate to a rearrangement reaction. After the reaction solution has been stirred for 4 hours at room temperature, it is evaporated. The syrup which remains is chromatographed on silica gel. Elution with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) gives a pale yellow viscous oil (Rf 0.39 on the abovementioned mixture as mobile phase), which is dissolved in dichloromethane and washed in succession with 75 ml of 5% hydrochloric acid and 75 ml of water. Evaporation to dryness of the organic solution which has been dried with Na₂SO₄ yields 1.05 g (63%) of pure 3-hydroxy-4,4-dimethyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone in the form of white crystals of melting point 75-77° C.

¹H NMR (d₆-DMSO, δ in ppm): 1.342, s, 6H: 2.088, t, J 9 Hz, 2H: 2.685, s, 3H: 2.982, t, J 9 Hz, 2H:8.030, d, J 8.1 Hz, 1H: 8.094, d, (J, 8.1 Hz), 1H.

Example H2 Preparation of 5-Methyl-5-trifluoromethylcyclohexane-1,3-dione (Compound H-B1066)

0.64 g of sodium were introduced into 40 ml of ethanol, and 3.23 ml of methyl acetoacetate and 4.9 g of isopropyl 4,4,4-trifluoro-3-methylbut-2-enoate were introduced, and the mixture was heated at the boil for 18 hours. After the mixture has been partitioned between dilute hydrochloric acid and ethyl acetate, the mixture is evaporated. The remaining unpurified methyl 2-methyl-4,6dioxo-2-trifluoromethylcyclohexanecarboxylate is hydrolysed in a mixture of methanol and water at boiling point in the presence of 9.1 g of sodium hydroxide.

The mixture is subsequently acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallization (ethyl acetate), pure 5-methyl-5-trifluoromethylcyclohexane-1,3-dione of melting point 150-152° C. is obtained.

Example H3 Preparation of Methyl 2-Hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate (Example H-B1069)

A 30% solution of 35.8 g of sodium methoxide is introduced into 65 ml of dimethyl sulfoxide and, within 20 minutes, treated with a mixture of 16.7 g of 3-methyl-3-butene-2-one and 32.4 g of dimethyl methoxymalonate at a temperature of 30-35° C. The mixture is stirred for 1 hour at a temperature of 35° C., and is then acidified with hydrochloric acid and extracted repeatedly with dichloromethane. The organic phases are washed with water, dried and concentrated. Crystallization from hot ethyl acetate and hexane gives pure methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate of melting point 117-117.5° C.

Example H4 Preparation of Methyl 2-Hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate (Compound A2-B1069)

2.23 g of fresh 2-methyl-6-trifluoromethylnicotinoyl chloride are added to a mixture of 2.14 g of methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate and 2.02 g of triethylamine in 30 ml of acetonitrile. After approximately 30 minutes, 0.065 g of potassium cyanide is added and the mixture is stirred for 18 hours. At pH 2, the mixture is subsequently partitioned between water and ethyl acetate, dried over magnesium sulfate and evaporated. Filtration on silica gel (mobile phase ethyl acetate/methanoltriethylamine 85:10:5) gives the pure methyl 2-hydroxy-1-methoxy-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate as a viscous oil.

Example H5 Preparation of 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone (Compound A2-B1070)

1.4 g of methyl 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate in dioxane/water (5:3) are treated with 0.586 g of potassium hydroxide and the mixture is stirred for 3 hours. The mixture is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography analogously to Example H4. 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone is obtained as a viscous oil (according to ¹H-NMR as a mixture of 3 tautomeric forms).

Example H6 5-Chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-cyclohex-4-ene-1,3-dione (Compound A2-B1105) and 6-[Chloro-(2-methyl-6-trifluoromethyl-pyridin-3-yl)methylene]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

7.0 g (55 mmol) of oxalyl chloride are introduced into 18.5 g (50 mmol) of 5-hydroxy-2,2,6,6-tetramethyl-4-2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (compound A2-B354), dissolved in 50 ml of dichloromethane; 5 drops of dimethylformamide are added, and the mixture is slowly heated up to boiling point. After approximately 30 minutes, after the evolution of gas has ceased, the mixture is evaporated and the product is crystallized by adding n-hexane. The main product obtained is pure 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione, m.p. 119.5-120° C. Further HPLC-separation of the mother liquor using 5-10% ethyl acetate in hexane gives the isomer 6[chloro-(2-methyl-6-trifluoromethylpyridine-3-yl)methylene]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione, m.p. 92.5-93° C.

Example H7 5-Chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (Compound A1210-B1105)

1.94 g (5 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione are treated in 20 ml of dichloroethane at a temperature of −10° C. with 0.94 g (10 mmol) of hydrogen peroxide/urea adduct and 1.89 g (9 mmol) of trifluoroacetic anhydride. The reaction mixture is warmed to room temperature, with stirring, and held for a further 4 hours at this temperature. The mixture is then partitioned between ethyl acetate and water of pH 5, washed with sodium chloride solution and evaporated. The residue which is filtered through silica gel is pure 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione of melting point 145.5-146° C.

Example H8 4-(2-Bromomethyl-6-trifluoromethylpyridine-3-carbonyl)-5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (Compound A1029-B1105)

0.39 g (1 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione and 0.20 g (1.1 mmol) of N-bromsuccinimide are refluxed in the presence of a catalytic amount of dibenzoyl peroxide in 10 ml of carbon tetrachloride. After the reaction has subsided, the resulting succinimide is removed by filtration and the crude product is purified by column chromatography (mobile phase: ethyl acetatelhexane 1:4). This gives pure 4-(2-bromomethyl-6-trifluoromethylpyridine-3-carbonyl)-5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione of melting point 94.5-95° C.

Example H9 2-(2-Acetoxymethyl-6-trifluoromethylpyridine-3-carbonyl)-4,4,6,6-tetramethyl-3,5-dioxocyclohex-1-enyl Acetate (Compound A1099-B1107)

0.4 g (1 mmol) of 5-chloro-2,2,6,6-tetramethyl-4-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-4-ene-1,3-dione (Example H7) is refluxed for 25 minutes in the presence of 3 ml of acetic anhydride. The mixture is then concentrated and partitioned between ethyl acetate and sodium bicarbonate solution at pH 6.5. The crude product, separated on silica gel (mobile phase: ethyl acetate/hexane 1:4) yields the pure 2-(2-acetoxymethyl-6-trifluormethylpyridine-3-carbonyl)-4,4,6,6-tetramethyl-3,5-dioxocyclohex-1-enyl acetate as an oil; ¹H-NMR (CDCl₃): 7.98 d, CH, 7.72 d, CH, 5.62 s, CH₂, 2.22 and 2.20 2×OAc, 1.58, s, 2×CH₃, 1.44 ppm, s, 2×CH₃.

Example H10 5-Hydroxy-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (Compound A2-D109) and 3-hydroxy-7-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohepta-2,6-dienone (Compound A2-F5)

0.82 g (2 mmol) of ethyl trans-5-hydroxy-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-oxobicyclo[4.1.0]hept-4-en-2-carboxylate (Compound A2-D111)is stirred in a 2:1 mixture of dioxane/water together with 0.254 g (4.5 mmol) of potassium hydroxide at room temperature until all of the starting material is reacted. Then, ethyl acetate is added, the mixture is acidified to pH 3 using 4 N HCl, and the 2-phase mixture is then heated for approx. 1 hour at a temperature of 40° C. The aqueous phase which is saturated with sodium chloride is then separated off. The ethyl acetate extract is evaporated to dryness and the product is chromatographed on silica gel (mobile phase ethyl acetate/hexane 1:2). The 1st fraction which is isolated is 3-hydroxy-7-methyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohepta-2,6-dienone as pure tautomer mixture, ¹H-NMR (CDCl₃): 17.72 and 17.08, 2s, OH, 7.6-7.45, 2 arom. H, 6.68 and 6.62, 2t, CH, 2.84, m, 2.63, m, 2.52, m, 4H, 2.62 and 2.54, 2s, CH₃, 2.03 and 1.77 ppm, 2s, CH₃. Subsequent elution with 100% ethyl acetate gives, as the 2nd fraction, the isomer and tautomer mixture of 5-hydroxy-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one, ¹H-NMR (CDCl₃): i.a. 17.62 and 17.48, 2s, OH, 7.6-7.45, 2 arom. H, 2.54, m, 2.48, 2s CH₃, 1.22 and 1.14, 2d, CH₃, 1.00 to 0.05 ppm, 2H.

Example H11 5-Hydroxy-2-methanesulfinyl-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (Compound A2-D114)

0.87 g (2.3 mmol) of 5-hydroxy-2-methyl-2-methylsulfanyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (Compound A2-D113), dissolved in 8 ml of methanol, is warmed for 3 hours at a temperature of 50° C. in the presence of 0.56 g of sodium periodate. The mixture is then partitioned between ethyl acetate an d sodium chloride solution, concentrated, and the crude product is purified by chromatography (mobile phase: ethyl acetate/m ethanol 19:1). Pure 5-hydroxy-2-methanesulfinyl-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one is obtained as tautomer and isomer mixture of melting point 159.5-160° C.

Example H12 2-Prop-2-ynyloxy-6-trifluoromethylnicotinic Acid (Compound A1025)

47 g (0.2 mol) of 2-oxo-6-trifluoromethyl-1,2-dihydropyridine-3-carboxylic acid, 20 ml (0.25 mol) of propargyl bromide and 43 g (0.31 mol) of potassium carbonate are heated to a temperature of 75° C. in a mixture of 40 ml of dimethylformamide and 80 ml of acetonitrile in the presence of a catalytic amount of 18-crown-6 ether. After 5 hours, the mixture is partitioned between ethyl acetate and saturated sodium chloride solution. The crude product is filtered through a silica gel column using 15% ethyl acetate in hexane. The main component, which is obtained in the form of an oil, is the pure ethyl 2-prop-2-ynyloxy-6-trifluoromethylnicotinate; ¹H-NMR (CDCl₃): 8.31, d, CH, 7.38, d, CH, 5.13, d, CH₂, 4.41, q, CH₂, 2.48, t, CCH, 1.41 ppm, t, CH₃. 36.3 g (0.13 mol) of this product is stirred over a period of 16 hours with a solution of 11.5 g (0.17 mol) of potassium hydroxide in 50 ml of water and 50 ml of dioxane. After acidification and extraction with ethyl acetate, crystalline 2-prop-2-ynyloxy-6-trifluoromethylnicotinic acid is obtained; ¹H-NMR (CDCl₃): 10.0, b, OH, 8.53, d, CH, 7.44, d, CH, 5.22, d, CH₂, 2.54 ppm, t, CCH.

Example H13 2-Methylthio-6-trifluoromethylnicotinic Acid (Compound A15)

9.4 g (40 mmol) of 2-oxo-6-trifluoromethyl-1,2-dihydropyridine-3-carboxylic acid are introduced into a 1-molar solution of 21.7 g of phosphorus tribromide (80 mmol) in dichloromethane at a temperature of 35° C. Then, the solvent is distilled off and the reaction mixture is heated slowly to boiling point, approx. 175° C. After 18 hours, the mixture is cooled to 0° C., diluted with dichloromethane and stirred with ice-water of pH 1.8. The organic phase is then washed with cold sodium carbonate solution and with 15% sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is ethyl 2-bromo-6-trifluoromethylnicotinate in the form of an oil; ¹H-NMR (CDCl₃): 8.20, d, CH, 7.72 d, CH, 4.46, q, CH₂, 1.42 ppm, t, CH₃ of melting point 164-166° C.

1.0 g (3.4 mmol) of this product, dissolved in a small amount of acetonitrile, is heated for 45 minutes to a temperature of 70° C. together with 0.26 g of sodium methanethiolate (3.4 mmol) in the presence of a catalytic amount of 1 5-crown-5 ether. The solution, which is cooled to room temperature, is then treated with 0.22 g (5.5 mmol) of sodium hydroxide and 5 ml of water, and stirring is continued for 3 hours. The neutral components are subsequently removed with a small amount of diethyl ether, and the aqueous phase is brought to pH 2.5 and extracted twice using ethyl acetate. This gives 2-methylthio-6-trifluoromethylnicotinic acid as crystalline product; ¹H-NMR (CDCl₃): 8.46, d, CH, 7.43, d, CH, 2.58 ppm, s, SCH₃.

Example H14 2-Methanesulfonylamino-6-trifluoromethylnicotinic Acid (Compound A1203)

0.52 g of methanesulfonamide is introduced into a tetrahydrofuran suspension of 0.24 g of 55% sodium hydride in oil. After the evolution of hydrogen has ceased, 1.5 g (5 mmol) of ethyl 2-bromo-6-trifluoromethylnicotinate, 0.3 g (5.2 mmol) of potassium fluoride and a catalytic amount of crown ether and 5 ml of N-methylpyrrolidone are added and the mixture is heated at the boil for 18 hours. The reaction mixture is then partitioned between ethyl acetate and water and freed from organic neutral constituents. The aqueous phase is brought to pH 2.9, extracted 3 times with fresh ethyl acetate, dried and concentrated. A crystalline product, ethyl 2-methanesulfonylamino-6-trifluoromethylnicotinate, is obtained from ether/hexane; ¹H-NMR (CDCl₃): 10.48, s, NH, 8.49, d, CH, 7.38, d, CH, 4.45, q, CH₂, 3.51, s, SO₂CH₃, 1.42 ppm, t, CH₃.

0.43 g (1.4 mmol) of the above product is hydrolysed at room temperature using a 1:1 solution of 0.22 g (3.9 mmol) of potassium hydroxide in dioxane/water. After the solution, which has been acidified to pH 2.5, has been extracted with ethyl acetate, 2-methanesulfonylamino-6-trifluoromethylnicotinic acid is obtained as crystallisate; ¹H-NMR (d₆-DMSO): 8.62, d, CH, 7.72, d, CH, 3.52 ppm, s, SO₂CH₃.

Example H15 (3-Methoxycarbonyl-6-trifluoromethylpyridin-2-ylmethyl)triphenylphosphonium bromide

50 g (0.23 mol) of methyl 2-methyl-6-trifluoromethylnicotinate and 49 g (0.28 mol) of N-bromosuccinimide are heated for 90 minutes at 50° C. in 500 ml of carbon tetrachloride in the presence of a catalytic amount of α,α-azaisobutyronitrile with illumination by a 150 watt lamp. Precipitated succinimide is filtered off, and the product methyl 2-bromomethyl-6-trifluoromethylnicotinate is then isolated as main component by means of column chromatography (mobile phase ethyl acetate/hexane 1:15), ¹H-NMR (CDCl₃): 4.01, s, 3H; 5.03, s, 2H; 7.72, d (J 8.2 Hz), 1H; 8.43 ppm, d, (J 8.2 Hz), 1H. 25.6 g (35 mmol) of the above product are taken up in toluene and treated with 10.6 g (40 mmol) of triphenylphosphine. After the mixture has been heated for 2 hours at boiling point, pure (3-methoxycarbonyl-6-trifluoromethylpyridine-2-ylmethyl)triphenylphosphonium bromide of melting point 215-217° C. crystallizes out upon cooling.

Example H16 2-Vinyl-6-trifluoromethylnicotinic Acid (Compound A21) and 2-(2,2-Dichloro-cycloproyl)-6-trifluoromethylnicotinic Acid (Compound A1092)

5.7 g (10 mmol) of (3-methoxycarbonyl-6-trifluoromethylpyridine-2-ylmethyl)triphenyl-phosphonium bromide are dissolved at room temperature in a 2-phase system of 25 ml of chloroform and 2.1 g (20 mmol) of sodium carbonate and reacted, in 10 ml of water, with a 35% aqueous solution of 1.7 g (20 mmol) of formaldehyde. After 1.5 hours, the organic phase is separated off and filtered through silica gel. Methyl 2-vinyl-6-trifluoromethylnicotinate is obtained as an oil, ¹H-NMR (CDCl₃): 8.31, d, CH, 7.10, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.68, dd, CH, 3.97 ppm, s, OCH₃.

0.97 g (4.1 mmol) of this product is again taken up in chloroform and reacted with 6 ml of 50% sodium hydroxide solution with vigorous stirring in the presence of 90 mg of benzyltrimethylammonium bromide. After 20 hours, the organic phase is separated off, concentrated and purified by HPLC (mobile phase: ethyl acetate/hexane 1:4). This gives pure methyl 2-(2,2-dichlorocyclopropyl)-6-trifluoromethylnicotinate, ¹H-NMR (CDCl₃): 8.50, d, CH, 7.70, d, CH, 4.08, s, OCH₃, 3.68, dd, CH, 2.64, dd, CH, 2.05 ppm, dd, CH.

Hydrolysis of the above esters gives, accordingly, the 2-vinyl-6-trifluoromethylnicotinic acid, ¹H-NMR (CDCl₃): 8.40, d, CH, 7.22, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.58 ppm, dd, CH, and 2-(2,2-dichlorocyclopropyl)-6-trifluoromethylnicotinic acid, ¹H-NMR (CDCl₃): 8.64, d, CH, 7.23, d, CH, 3.78, dd, CH, 2,67, dd, CH, 2,08 ppm, dd, CH.

Example H17 2-Propa-1,2-dienyl-6-trifluoromethylnicotinic Acid (A1096) and 2-(3-Chloro-propenyl)-6-trifluoromethylnicotinic Acid (Compound A1095)

6.7 g (11 mmol) of ((3-methoxycarbonyl-6-trifluoromethylpyridin-2-yl)methyl)triphenyl-phosphonium bromide are reacted with 2 ml of 45% aqueous chloroacetaldehyde solution (14 mmol) and 1.5 g (14 mmol) of sodium carbonate with vigorous stirring in a 2-phase system of 20 ml of chloroform and 7 ml of water. After 2 hours, the organic solution is separated off and washed with half-saturated sodium chloride solution. The product is separated on silica gel (mobile phase ethyl acetatelhexane 1:4). As the 1 st fraction, methyl 2-propa-1,2-dienyl-6-trifluoromethylnicotinate, ¹H-NMR (CDCl₃): 7.62, m, CH, 7.55, d, CH, 7.32, d, CH, 7.04, d, CH, 7.02, m, CH, 3.98 ppm, s, OCH₃, is isolated, and methyl 2-(3-chloropropenyl)-6-trifluoromethylnicotinate, ¹H-NMR (CDCl₃): 8.85, d, CH, 7.65, dd, 7.58, d, CH, CH, 7.28, dd, CH, 4.32, d, CH₂Cl, 3.98 ppm, s, OCH₃ is isolated as the 2nd fraction.

Hydrolysis of the above esters gives 2-propa-1,2-dienyl-6-trifluoromethylnicotinic acid, m.p. 194-196° C., and 2-(3-chloropropenyl)-6-trifluoromethylnicotinic acid, m.p. 137-138° C.

Example H18 2-Chloro-4-methyl-6-trifluoromethylnicotinic Acid (Compound A1205)

In a pressurized vessel, 7.5 g (0.03 mol) of ((3-ethoxycarbonyl)-4-methyl-6-trifluoromethyl)-pyrid-2-one is heated for 3 hours at a temperature of 170° C. in the presence of 5.8 ml of phenyl dichlorophosphate. When cold, the reaction solution is filtered directly over a short silica gel column (mobile phase: ethyl acetate/hexane 1:9), and the 2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylethyl ester is obtained as oily product. The latter is hydrolysed in the presence of aqueous potassium hydroxide solution in dioxane at a temperature of 40° C. After acidification to pH 2.7, extraction with ethyl acetate gives 2-chloro-4-methyl-6-trifluoromethylnicotinic acid as crystalline product: ¹H NMR (CDCl₃): 9.55, b, OH, 7.55, s, 1H; 3.80, s, CH₃, 2.56 ppm, s, CH₃.

Example H19 4-Methyl-6-trifluoromethylnicotinic Acid (Compound A531)

To a suspension of 0.55 g of 10% Pd/C in 20 ml of methanol there are added 3.0 g (16.8 mmol) of the 2-chloro-4-methyl-6-trifluoromethylpyridin-3-ylethyl ester and, in 2 portions, a total of 5 g of ammonium formate, and the mixture is stirred for 24 hours at room temperature. The reaction mixture is then filtered through Celite and partitioned between ethyl acetate and sodium chloride solution. Chromatographic purification (mobile phase 1:9) gives the 4-methyl-6-trifluoromethylpyridin-3-ylethyl ester in the form of an oil: hydrolysis in accordance with the above processes gives 4-methyl-6-trifluoromethylnicotinic acid: ¹H NMR (CDCl₃): 9.32, s, 1H, 7.62, s, 1H, 2.79 ppm, s, CH₃.

Example H20 5-Methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione (Compound H-D113)

A 1-molar solution of 16.7 g (0.1 mol) of lithium bistrimethylsilylamide in tetrahydrofuran is added at a temperature of 0° C. to a solution of 13.4 g (0.1 mol) of methyl 2-methylmercaptopropionate in 30 ml of tetrahydrofuran. After the mixture has been stirred for 1 hour, 11.8 g (0.1 mol) of 5-chloropent-3-en-2-one are added dropwise in the course of 20 minutes in such a way that the temperature can be maintained at 0° C. After the mixture has been stirred for a further 30 minutes, ice-water is added, and the mixture is acidified with hydrochloric acid and extracted with diethyl acetate. The crude product is chromatographed with ethyl acetate/hexane 15/85. This gives methyl 2-(2-acetylcyclopropyl)-2-methylsulfanylpropionate, ¹H-NMR (CDCl₃): 3.74, s, OCH₃, 2.19 and 2.14, 2s, SCH₃, 2.12, and 2.00, 2s, CH₃, 2.2-1.9, 1H, 1.3, s, CH₃, 1.3 to 1.0 ppm, 2H, as a 3:7 isomer mixture.

2.45 g (11 mmol) of the above product, which is enriched in the more polar isomer, is heated with 4.5 g (25 mmol) of 30% sodium ethoxide solution in a mixture of toluene/dimethylformamide 19:1 for 90 minutes at 115° C. The mixture is then taken up in ethyl acetate and washed with dilute hydrochloric acid at pH 3. The residue which has been isolated is purified on silica gel (mobile phase ethyl acetate/hexane 1:2). This gives the isomer I of 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione, ¹H-NMR (CDCl₃): 3.48, d, CH, 3.00 d, CH, 2.21, m, CH, 1.94, m, CH, 1.86, s, CH₃, 1.57, s, CH₃, 1.44, m, CH, 1.04 ppm, m, CH.

The isomer II of 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione, ¹H-NMR (CDCl₃): 3.78, d, CH, 3.14 d, CH, 2.22, m, CH, 1.93, m, CH, 2.08, s, CH₃, 1.58, s, CH₃, 1.6-1.4 ppm, 2H, is obtained from the product which is enriched in apolar isomers.

Example H21 4-Methylcyclohept-4-ene-1,3-dione (Compound H-F5)

1.0 g (5.4 mmol) of the 5-methyl-5-methylsulfanylbicyclo[4.1.0]heptane-2,4-dione isomers II is hydrogenated for 90 minutes under atmospheric pressure in 15 ml of methanol in the presence of 5 g Raney nickel. The mixture is concentrated and purified over silica gel (mobile phase ethyl acetatelhexane 1:1), and 4-methylcyclohept-4-ene-1,3-dione, ¹H-NMR (CDCl₃): 6.84, m, CH, 3.94, s, CH₂, 2.77, m, CH₂, 2,59, m, CH₂, 1.88 ppm, s, CH₃, is obtained as an oil.

Example H22 2-Oxaspiro[4.5]decane-1,6,8-trione (Compound H-E16)

A suspension of sodium hydride (55% in oil, 27.5 mmol) in 70 ml of anhydrous tetrahydroturan is cooled to a temperature of −20° C., and a solution of 2-acylbutyrolactone (2.69 ml, 25 mmol) in 5 ml of tetrahydrofuran is subsequently added dropwise. After the reaction mixture has been stirred for 1 hour at this temperature, it is treated dropwise with a solution of methyl acrylate (4.5 ml, 50 mmol) in tetrahydrofuran at a temperature of −20° C. The reaction mixture is subsequently allowed to warm to room temperature and is stirred for 8 hours. The mixture is then poured into ice-water and acidified with 2 N hydrochloric acid to pH 1. After extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo, the product is purified by flash chromatography (eluent: ethyl acetate/acetic acid 1:1). This gives 2-oxaspiro[4.5]decane-1,6,8-trione in the form of a white powder of melting point 145-148° C.

Example H23 Spiro[2.5]octane-4,6-dione (Compound H-C1)

3.4 g of sodium hydride (55% suspension in oil, 78.0 mmol) were introduced into 1 l of tert-butanol and the mixture was stirred for a few minutes at room temperature. Then, 2-acylbutyrolactone (100 g, 0.78 mol) is added and the reaction mixture is treated with methyl acrylate (67.2 g, 0.78 mmol) over a period of 3.5 hours at a temperature of approx. 30° C. The reaction mixture is taken up in diethyl ether and washed in succession with 75 ml of saturated NaH₂PO₄ solution, water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. This gives 162 g of methyl 3-(3-acetyl-2-oxotetrahydrofuran-3-yl)propionate as colourless oil, which can be reacted further without purification.

2.0 g (9.3 mmol) of the above product and 2.1 g of sodium iodide (14.0 mmol) are dissolved in 10 ml of 1,3-dimethyl-2-imidazolidinone and the solution is heated for 3 hours at 210° C. After cooling, the reaction mixture is poured into dilute aqueous saturated NaH₂PO₄ solution and extracted with diethyl ether, dried over sodium sulfate and concentrated. This gives methyl 3-(1-acetylcyclopropyl)propionate as a colourless oil.

74.5 g of methyl 3-(1-acetylcyclopropyl)propionate (0.32 mol) are dissolved in 1 l of tetrahydrofuran and the solution is treated portionwise with 14.3 g of sodium hydride (55% suspension in oil, 0.32 mol) at room temperature. After 1 hour, the reaction mixture is diluted with 200 ml of dimethylformamide and warmed to 70° C. After 8 hours, tetrahydrofuran is removed in vacuo, and the residue is poured into 2 N hydrochloric acid and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated, and column chromatography over silica gel (methylene chloride:ethanol 9:1 as eluent) gives spiro[2.5]octane-4,6-dione in the form of white crystals of melting point 116-118° C.

Example H24 2-(4,6-Dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethylnicotinic Acid (Compound A1088)

2.0 g (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethylnicotinate (prepared analogously to Heterocycles, 46, 129 (1997) by heating methyl 4-chloro-3-oxobutyrate and 4-amino-1,1,1-trifluorobut-3-en-2-one in toluene in the presence of trifluoroacetic acid) are introduced into 30 ml of acetonitrile and 1.63 g (11.83 mmol) of K₂CO₃ and reacted with 1.49 g (8.67 mmol) of 4,6-dimethoxypyrimidin-2-thiol at room temperature. After 4 hours, the mixture is poured into ethyl acetate/water, the ethyl acetate phase is removed, and the aqueous phase is reextracted with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulfate, concentrated and purified by recrystallization from ethyl acetate/hexane. This gives methyl 2-(4,6-dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethylnicotinate in the form of white crystals of melting point 123-124° C.

Hydrolysis of the above esters (analogously to Example H1) gives, accordingly, 2-(4,6-dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethynicotinic acid in the form of white crystals of melting point 157-158° C. ¹H-NMR (CDCl₃): 3.96, s, 6H; 3.99, s, 3H; 5.03, s, 2H; 5.72, s, 1H; 7.66, d (J, 8.1 Hz), 1H; 8.40 ppm, d (J, 8.1 Hz), 1H.

Example H25 2-Cyanomethyl-6-trifluoromethylnicotinic Acid (Compound A1103)

2.0 g (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethylnicotinate and 565 mg (8.67 mmol) of potassium cyanide are reacted in 20 ml of acetonitrile/water mixture (1:1) in the presence of 270 mg of tetrabutylammonium hydrogen sulfate. After the reaction has ended, the mixture is poured into water and extracted with ethyl acetate. After the ethyl acetate phase has been dried over sodium sulfate and concentrated, the crude product is purified by means of HPLC (ethyl acetate: hexane as eluent). This gives 610 mg (32% of theory) of methyl 2-cyanomethyl-6-trifluoromethylnicotinate in the form of an oil. ¹H-NMR (CDCl₃): 3.96, s, 3H; 4.38, s, 2H; 7.72, d (J, 8.1 Hz), 1H; 8.48 ppm, d (J, 8.1 Hz), 1H.

Hydrolysis analogous to the methods already mentioned above yields 2-cyanomethyl-6-trifluoromethylnicotinic acid in the form of yellow crystals of melting point 152-153° C. ¹H-NMR (CDCl₃): 4.18, s, 2H; 7.72, d (J, 8.1 Hz), 1H; 8.52 ppm, d (J, 8.1 Hz), 1H.

Example H26 3-(6-Difluoromethyl-2-methyloyridine-3-carbonyl)-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate (Compound A124-B34)

200 mg (0.516 mmol) of methyl 3-[6-(chlorodifluoromethyl)-2-methylpyridine-3-carbonyl]-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate (compound A94-B34) is heated for 3 hours at a temperature of 120° C. in 8 ml of toluene in the presence of 0.18 ml (0.62 mmol) tris(trimethylsilyl)silane. The viscous residue which remains is chromatographed on silica gel. The pale yellow viscous oil which is obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 by volume) is dissolved in dichloromethane and washed in succession with aqueous hydrochloric acid and water. Evaporation of the organic solution which has been dried with Na₂SO₄ yields 140 mg (73%) of pure methyl 3-(6-difluoromethyl-2-methylpyridine-3-carbonyl)-2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate in the form of a pale yellow oil. ¹H-NMR (CDCl₃): 1.28, s, 3H; 1.79-1.97, m, 1H; 2.39-2.46, m, 1H; 2.43, s, 3H; 2.69, dt (J, 19.2 and 4.8 Hz), 1H; 2.82-2.92, m, 1H; 3.67, s, 3H; 6.55, t, (J, 55.5 Hz), 1H; 7.43, d (J, 7.8 Hz), 1H; 7.49, d (J, 7.8 Hz), 1H; 17.20 ppm, br s, 1H.

Example H27 3-Hydroxy-2-(2-methyl-1-oxy-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Compound A1210-B1)

16.1 g (0.054 mol) of 3-hydroxy-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Example A2-B1) and 10.2 g (0.11 mol) of urea/hydrogen peroxide complex are dissolved in 150 ml of methylene chloride, and 22.1 ml (0.162 mol) of trifluoroacetic anhydride are subsequently added dropwise at a temperature of 25° C. After the reaction mixture has been stirred for 14 hours at a temperature of 25° C., it is poured into ethyl acetate and water, and the organic phase is washed twice with water, dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel (eluent: ethyl acetate/methanol 9/1). This gives 2.4 g (14%) of the desired product in the form of white crystals (m.p. 117-119° C). ¹H-NMR (d₆-DMSO): 1.98, m, 2H; 2.30, s, 3H; 2.60, t (J, 7.25 Hz), 4H: 7.32, d(J, 9.8 Hz), 1H; 7.92 ppm, d (J, 9.8 Hz), 1H.

Example H28 2-(2-Methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcylohex-2-enone (Compound A2-B1102)

4.0 g (0.0134 mol) of 3-hydroxy-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (compound A2-B1) are suspended in 25 ml of oxalyl chloride, and 0.1 ml of dimethylformamide is subsequently added dropwise. After the vigorous evolution of gas has ceased, the mixture is held for 1.5 hours at a bath temperature of 45° C. and subsequently concentrated, and the residue (3-chloro-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-cyclohex-2-enone) is dissolved in 60 ml of methylene chloride. Triethylamine (3.7 ml, 0.0268 mol), dimethylaminopyridine (160 mg, 1.34 mmol) and 1.5 ml (0.0147 mol) of thiophenol are added at a temperature of 0-5° C. After 20 hours at a temperature of 22° C., the reaction mixture is concentrated and purified on silica gel (hexane/ethyl acetate 5:1). Trituration in hexane gives pure 2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone in the form of white crystals of melting point 124-125° C. ¹H-NMR (CDCl₃): 1.99, m, 2H; 2.41, m 4H; 2.80, s, 3H; 2.60: 7.40-7.60, m, 6H; 7.80 ppm, d(J, 8.2 Hz), 1H.

Example H29 3-Benzenesulfonyl-2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)cyclohex-2-enone (Compound A2-B1104)

0.8 g (0.00204 mol) of the 2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone obtained above is dissolved in 30 ml of methylene chloride, and 1.39 ml of peracetic acid (39% in acetic acid, 0.00816 mol) are subsequently added dropwise at a temperature of 25° C. After 4 hours at 25° C., the reaction mixture is poured into ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. Filtration gives 0.72 g (84% of theory) of 3-benzenesulfonyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone in the form of white crystals of melting point 165-167° C. ¹H-NMR (CDCl₃): 2.30, m, 2H; 2.55, t (J, 7 Hz), 2H; 2.71, m, 2H; 3.05, s, 3H;: 7.40-7.80, m, 4H; 7.80-8.05 ppm, m, 3H.

Example H30 6-Difluoromethyl-2-methylnicotinic Acid (Compound A124)

6.1 g (0.026 mol) of methyl 6-(chlorodifluoromethyl)-2-methylnicotinate (prepared analogously to Heterocycles, 46, 129 (1997) by heating methyl 3-oxobutyrate and 4-amino-1-chloro-1,1-difluorobut-3-en-2-one in toluene in the presence of trifluoroacetic acid) is heated at a temperature of 120° C. in the presence of 430 mg (0.26 mol) of tris(trimethylsilyl)silane in 150 ml of toluene. After 1.5 hours, the reaction mixture is concentrated and purified on silica gel (hexane/ethyl acetate 13:1). This gives 3.8 g (73% of theory) of methyl 6-difluoromethyl-2-methylnicotinate as colourless oil.

Hydrolysis of the above esters (analogously to Example H1) gives, accordingly, 6-difluoromethyl-2-methylnicotinic acid in the form of white crystals of melting point 135-136° C. ¹H-NMR (CDCl₃): 2.68, s, 3H; 6.583, t (J, 55.2 Hz), 1H;: 7.54, d (J, 8.1 Hz), 1H; 7.54 ppm, d (J, 8.1 Hz), 1H.

Example H31 6-(Chlorodifluoromethyl)-2-methylnicotinic Acid (Compound A-94)

5.0 g (18.62 mmol) of methyl 2-methyl-6-trichloromethylnicotinate (prepared analogously to Heterocycles, 46, 129 (1997)) are cooled to a temperature of −40° C. in a pressurized container, and 35 g (1.75 mol) of distilled hydrofluoric acid are subsequently passed in at this temperature. The mixture is heated for 10 hours at 200° C. (pressure approx. 55 bar). After cooling, the pressure is released using a gas-washing system, HF is removed by suction, and the reaction mixture is poured into ethyl acetate/ice. The ethyl acetate phase is separated off, and the aqueous phase is reextracted using ethyl acetate. The combined ethyl acetate phases are washed with water, dried over sodium sulfate and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. Filtration gives 2.2 g (53% of theory) of 6-chlorodifluoromethyl-2-methylnicotinic acid as pale green crystals of melting point 134-135° C.

¹H-NMR (CDCl₃): 2.987, s, 3H; 7.64, d (J, 8.1 Hz), 1H; 8.513 ppm, d (J, 8.1 Hz), 1H.

Example H32 2-[2-(4,6-Dimethoxypyrimidine-2-sulfonylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone (Compound A1090-B1)

100 mg of 2-[2-(4,6-dimethoxypyrimidin-2-ylsulfanylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone (compound A1088-B1) are dissolved in methylene chloride, and 0.3 ml of peracetic acid (39% in acetic acid) is subsequently added dropwise at a temperature of 25° C. After 15 hours at 25° C., the reaction mixture is poured into ethyl acetate and water, and the organic phase is washed with water, dried with sodium sulfate and concentrated. This gives 95 mg of 2-[2-(4,6-dimethoxypyrimidine-2-sulfonylmethyl)-6-trifluoromethylpyridine-3-carbonyl]-3-hydroxycyclohex-2-enone in the form of a resin. ¹H-NMR (CDCl₃): 3.79, s, 6H; 3.91, s, 3H; 4.99, s, 2H; 6.09, s, 1H; 7.52, d (J, 9 Hz), 1H; 7.68 ppm, d (J, 9 Hz), 1H.

In the tables which follow, Ph is the phenyl group and CC an ethyne group.

TABLE 1 Compounds of the formula XVId: (XVId)

Comp. No. R₂ R₃ R₄ R₅ p A1  H H H CF₃ 0 A2  CH₃ H H CF₃ 0 A3  CH₃CH₂ H H CF₃ 0 A4  (CH₃)₂CH H H CF₃ 0 A5  (CH₃)₃C H H CF₃ 0 A6  cyclopropyl H H CF₃ 0 A7  CH₃(CH₂)₂ H H CF₃ 0 A8  CH₃OCH₂ H H CF₃ 0 A9  CH₃O(CH₂)₂ H H CF₃ 0 A10  Ph H H CF₃ 0 A11  PhO H H CF₃ 0 A12  PhS H H CF₃ 0 A13  PhSO H H CF₃ 0 A14  PhSO₂ H H CF₃ 0 A15  CH₃S H H CF₃ 0 A16  CH₃SO H H CF₃ 0 A17  CF₃ H H CF₃ 0 A18  F₂CH H H CF₃ 0 A19  HCC H H CF₃ 0 A20  CH₃CC H H CF₃ 0 A21  CH₂═CH H H CF₃ 0 A22  CH₂═CHCH₂ H H CF₃ 0 A23  CH₃SO₂N(CH₃) H H CF₃ 0 A24  (CH₃)₂N H H CF₃ 0 A25  (CH₃)₂NSO₂ H H CF₃ 0 A26  ClCH₂ H H CF₃ 0 A27  CH₃SCH₂ H H CF₃ 0 A28  CH₃SOCH₂ H H CF₃ 0 A29  CH₃SO₂CH₂ H H CF₃ 0 A30  [1.2.4]-triazol-1-ylmethyl H H CF₃ 0 A31  CH₃ CF₃ H CH₃ 0 A32  CH₃ CH₃ H CF₃ 0 A33  H H H CF₃CF₂ 0 A34  CH₃ H H CF₃CF₂ 0 A35  CH₃CH₂ H H CF₃CF₂ 0 A36  cyclopropyl H H CF₃CF₂ 0 A37  (CH₃)₃C H H CF₃CF₂ 0 A38  (CH₃)₂CH H H CF₃CF₂ 0 A39  CH₃(CH₂)₂ H H CF₃CF₂ 0 A40  CH₃OCH₂ H H CF₃CF₂ 0 A41  CH₃O(CH₂)₂ H H CF₃CF₂ 0 A42  Ph H H CF₃CF₂ 0 A43  PhO H H CF₃CF₂ 0 A44  PhS H H CF₃CF₂ 0 A45  PhSO H H CF₃CF₂ 0 A46  PhSO₂ H H CF₃CF₂ 0 A47  CH₃S H H CF₃CF₂ 0 A48  CH₃SO H H CF₃CF₂ 0 A49  CF₃ H H CF₃CF₂ 0 A50  F₂CH H H CF₃CF₂ 0 A51  HCC H H CF₃CF₂ 0 A52  CH₃CC H H CF₃CF₂ 0 A53  CH₂═CH H H CF₃CF₂ 0 A54  CH₂═CHCH₂ H H CF₃CF₂ 0 A55  CH₃SO₂N(CH₃) H H CF₃CF₂ 0 A56  (CH₃)₂N H H CF₃CF₂ 0 A57  (CH₃)₂NSO₂ H H CF₃CF₂ 0 A58  ClCH₂ H H CF₃CF₂ 0 A59  CH₃SCH₂ H H CF₃CF₂ 0 A60  CH₃SOCH₂ H H CF₃CF₂ 0 A61  CH₃SO₂CH₂ H H CF₃CF₂ 0 A62  [1.2.4]-triazol-1-ylmethyl H H CF₃CF₂ 0 A63  H H H CF₃CF₂CF₂ 0 A64  CH₃ H H CF₃CF₂CF₂ 0 A65  CH₃CH₂ H H CF₃CF₂CF₂ 0 A66  cyclopropyl H H CF₃CF₂CF₂ 0 A67  (CH₃)₃C H H CF₃CF₂CF₂ 0 A68  (CH₃)₂CH H H CF₃CF₂CF₂ 0 A69  CH₃(CH₂)₂ H H CF₃CF₂CF₂ 0 A70  CH₃OCH₂ H H CF₃CF₂CF₂ 0 A71  CH₃O(CH₂)₂ H H CF₃CF₂CF₂ 0 A72  Ph H H CF₃CF₂CF₂ 0 A73  PhO H H CF₃CF₂CF₂ 0 A74  PhS H H CF₃CF₂CF₂ 0 A75  PhSO H H CF₃CF₂CF₂ 0 A76  PhSO₂ H H CF₃CF₂CF₂ 0 A77  CH₃S H H CF₃CF₂CF₂ 0 A78  CH₃SO H H CF₃CF₂CF₂ 0 A79  CF₃ H H CF₃CF₂CF₂ 0 A80  F₂CH H H CF₃CF₂CF₂ 0 A81  HCC H H CF₃CF₂CF₂ 0 A82  CH₃CC H H CF₃CF₂CF₂ 0 A83  CH₂═CH H H CF₃CF₂CF₂ 0 A84  CH₂═CHCH₂ H H CF₃CF₂CF₂ 0 A85  CH₃SO₂N(CH₃) H H CF₃CF₂CF₂ 0 A86  (CH₃)₂N H H CF₃CF₂CF₂ 0 A87  (CH₃)₂NSO₂ H H CF₃CF₂CF₂ 0 A88  ClCH₂ H H CF₃CF₂CF₂ 0 A89  CH₃SCH₂ H H CF₃CF₂CF₂ 0 A90  CH₃SOCH₂ H H CF₃CF₂CF₂ 0 A91  CH₃SO₂CH₂ H H CF₃CF₂CF₂ 0 A92  [1.2.4]-triazol-1-ylmethyl H H CF₃CF₂CF₂ 0 A93  H H H CF₂Cl 0 A94  CH₃ H H CF₂Cl 0 A95  CH₃CH₂ H H CF₂Cl 0 A96  cyclopropyl H H CF₂Cl 0 A97  (CH₃)₃C H H CF₂Cl 0 A98  (CH₃)₂CH H H CF₂Cl 0 A99  CH₃(CH₂)₂ H H CF₂Cl 0 A100 CH₃OCH₂ H H CF₂Cl 0 A101 CH₃O(CH₂)₂ H H CF₂Cl 0 A102 Ph H H CF₂Cl 0 A103 PhO H H CF₂Cl 0 A104 PhS H H CF₂Cl 0 A105 PhSO H H CF₂Cl 0 A106 PhSO₂ H H CF₂Cl 0 A107 CH₃S H H CF₂Cl 0 A108 CH₃SO H H CF₂Cl 0 A109 CF₃ H H CF₂Cl 0 A110 F₂CH H H CF₂Cl 0 A111 HCC H H CF₂Cl 0 A112 CH₃CC H H CF₂Cl 0 A113 CH₂═CH H H CF₂Cl 0 A114 CH₂═CHCH₂ H H CF₂Cl 0 A115 CH₃SO₂N(CH₃) H H CF₂Cl 0 A116 (CH₃)₂N H H CF₂Cl 0 A117 (CH₃)₂NSO₂ H H CF₂Cl 0 A118 ClCH₂ H H CF₂Cl 0 A119 CH₃SCH₂ H H CF₂Cl 0 A120 CH₃SOCH₂ H H CF₂Cl 0 A121 CH₃SO₂CH₂ H H CF₂Cl 0 A122 [1.2.4]-triazol-1-ylmethyl H H CF₂Cl 0 A123 H H H CHF₂ 0 A124 CH₃ H H CHF₂ 0 A125 CH₃CH₂ H H CHF₂ 0 A126 cyclopropyl H H CHF₂ 0 A127 (CH₃)₃C H H CHF₂ 0 A128 (CH₃)₂CH H H CHF₂ 0 A129 CH₃(CH₂)₂ H H CHF₂ 0 A130 CH₃OCH₂ H H CHF₂ 0 A131 CH₃O(CH₂)₂ H H CHF₂ 0 A132 Ph H H CHF₂ 0 A133 PhO H H CHF₂ 0 A134 PhS H H CHF₂ 0 A135 PhSO H H CHF₂ 0 A136 PhSO₂ H H CHF₂ 0 A137 CH₃S H H CHF₂ 0 A138 CH₃SO H H CHF₂ 0 A139 CF₃ H H CHF₂ 0 A140 F₂CH H H CHF₂ 0 A141 HCC H H CHF₂ 0 A142 CH₃CC H H CHF₂ 0 A143 CH₂═CH H H CHF₂ 0 A144 CH₂═CHCH₂ H H CHF₂ 0 A145 CH₃SO₂N(CH₃) H H CHF₂ 0 A146 (CH₃)₂N H H CHF₂ 0 A147 (CH₃)₂NSO₂ H H CHF₂ 0 A148 ClCH₂ H H CHF₂ 0 A149 CH₃SCH₂ H H CHF₂ 0 A150 CH₃SOCH₂ H H CHF₂ 0 A151 CH₃SO₂CH₂ H H CHF₂ 0 A152 [1.2.4]-triazol-1-ylmethyl H H CHF₂ 0 A153 H H H CCl₃ 0 A154 CH₃ H H CCl₃ 0 A155 CH₃CH₂ H H CCl₃ 0 A156 cyclopropyl H H CCl₃ 0 A157 (CH₃)₃C H H CCl₃ 0 A158 (CH₃)₂CH H H CCl₃ 0 A159 CH₃(CH₂)₂ H H CCl₃ 0 A160 CH₃OCH₂ H H CCl₃ 0 A161 CH₃O(CH₂)₂ H H CCl₃ 0 A162 Ph H H CCl₃ 0 A163 PhO H H CCl₃ 0 A164 PhS H H CCl₃ 0 A165 PhSO H H CCl₃ 0 A166 PhSO₂ H H CCl₃ 0 A167 CH₃S H H CCl₃ 0 A168 CH₃SO H H CCl₃ 0 A169 CF₃ H H CCl₃ 0 A170 F₂CH H H CCl₃ 0 A171 HCC H H CCl₃ 0 A172 CH₃CC H H CCl₃ 0 A173 CH₂═CH H H CCl₃ 0 A174 CH₂═CHCH₂ H H CCl₃ 0 A175 CH₃SO₂N(CH₃) H H CCl₃ 0 A176 (CH₃)₂N H H CCl₃ 0 A177 (CH₃)₂NSO₂ H H CCl₃ 0 A178 ClCH₂ H H CCl₃ 0 A179 CH₃SCH₂ H H CCl₃ 0 A180 CH₃SOCH₂ H H CCl₃ 0 A181 CH₃SO₂CH₂ H H CCl₃ 0 A182 [1.2.4]-triazol-1-ylmethyl H H CCl₃ 0 A183 H H CH₃ CF₃ 0 A184 CH₃ H CH₃ CF₃ 0 A185 CH₃CH₂ H CH₃ CF₃ 0 A186 cyclopropyl H CH₃ CF₃ 0 A187 (CH₃)₃C H CH₃ CF₃ 0 A188 (CH₃)₂CH H CH₃ CF₃ 0 A189 CH₃(CH₂)₂ H CH₃ CF₃ 0 A190 CH₃OCH₂ H CH₃ CF₃ 0 A191 CH₃O(CH₂)₂ H CH₃ CF₃ 0 A192 Ph H CH₃ CF₃ 0 A193 PhO H CH₃ CF₃ 0 A194 PhS H CH₃ CF₃ 0 A195 PhSO H CH₃ CF₃ 0 A196 PhSO₂ H CH₃ CF₃ 0 A197 CH₃S H CH₃ CF₃ 0 A198 CH₃SO H CH₃ CF₃ 0 A199 CF₃ H CH₃ CF₃ 0 A200 F₂CH H CH₃ CF₃ 0 A201 HCC H CH₃ CF₃ 0 A202 CH₃CC H CH₃ CF₃ 0 A203 CH₂═CH H CH₃ CF₃ 0 A204 CH₂═CHCH₂ H CH₃ CF₃ 0 A205 CH₃SO₂N(CH₃) H CH₃ CF₃ 0 A206 (CH₃)₂N H CH₃ CF₃ 0 A207 (CH₃)₂NSO₂ H CH₃ CF₃ 0 A208 ClCH₂ H CH₃ CF₃ 0 A209 CH₃SCH₂ H CH₃ CF₃ 0 A210 CH₃SOCH₂ H CH₃ CF₃ 0 A211 CH₃SO₂CH₂ H CH₃ CF₃ 0 A212 H H CH₃ CF₃CF₂ 0 A213 CH₃ H CH₃ CF₃CF₂ 0 A214 CH₃CH₂ H CH₃ CF₃CF₂ 0 A215 cyclopropyl H CH₃ CF₃CF₂ 0 A216 (CH₃)₃C H CH₃ CF₃CF₂ 0 A217 (CH₃)₂CH H CH₃ CF₃CF₂ 0 A218 CH₃(CH₂)₂ H CH₃ CF₃CF₂ 0 A219 CH₃OCH₂ H CH₃ CF₃CF₂ 0 A220 CH₃O(CH₂)₂ H CH₃ CF₃CF₂ 0 A221 Ph H CH₃ CF₃CF₂ 0 A222 PhO H CH₃ CF₃CF₂ 0 A223 PhS H CH₃ CF₃CF₂ 0 A224 PhSO H CH₃ CF₃CF₂ 0 A225 PhSO₂ H CH₃ CF₃CF₂ 0 A226 CH₃S H CH₃ CF₃CF₂ 0 A227 CH₃SO H CH₃ CF₃CF₂ 0 A228 CF₃ H CH₃ CF₃CF₂ 0 A229 F₂CH H CH₃ CF₃CF₂ 0 A230 HCC H CH₃ CF₃CF₂ 0 A231 CH₃CC H CH₃ CF₃CF₂ 0 A232 CH₂═CH H CH₃ CF₃CF₂ 0 A233 CH₂═CHCH₂ H CH₃ CF₃CF₂ 0 A234 CH₃SO₂N(CH₃) H CH₃ CF₃CF₂ 0 A235 (CH₃)₂N H CH₃ CF₃CF₂ 0 A236 (CH₃)₂NSO₂ H CH₃ CF₃CF₂ 0 A237 ClCH₂ H CH₃ CF₃CF₂ 0 A238 CH₃SCH₂ H CH₃ CF₃CF₂ 0 A239 CH₃SOCH₂ H CH₃ CF₃CF₂ 0 A240 CH₃SO₂CH₂ H CH₃ CF₃CF₂ 0 A241 H H CH₃ CF₃CF₂CF₂ 0 A242 CH₃ H CH₃ CF₃CF₂CF₂ 0 A243 CH₃CH₂ H CH₃ CF₃CF₂CF₂ 0 A244 cyclopropyl H CH₃ CF₃CF₂CF₂ 0 A245 (CH₃)₃C H CH₃ CF₃CF₂CF₂ 0 A246 (CH₃)₂CH H CH₃ CF₃CF₂CF₂ 0 A247 CH₃(CH₂)₂ H CH₃ CF₃CF₂CF₂ 0 A248 CH₃OCH₂ H CH₃ CF₃CF₂CF₂ 0 A249 CH₃O(CH₂)₂ H CH₃ CF₃CF₂CF₂ 0 A250 Ph H CH₃ CF₃CF₂CF₂ 0 A251 PhO H CH₃ CF₃CF₂CF₂ 0 A252 PhS H CH₃ CF₃CF₂CF₂ 0 A253 PhSO H CH₃ CF₃CF₂CF₂ 0 A254 PhSO₂ H CH₃ CF₃CF₂CF₂ 0 A255 CH₃S H CH₃ CF₃CF₂CF₂ 0 A256 CH₃SO H CH₃ CF₃CF₂CF₂ 0 A257 CF₃ H CH₃ CF₃CF₂CF₂ 0 A258 F₂CH H CH₃ CF₃CF₂CF₂ 0 A259 HCC H CH₃ CF₃CF₂CF₂ 0 A260 CH₃CC H CH₃ CF₃CF₂CF₂ 0 A261 CH₂═CH H CH₃ CF₃CF₂CF₂ 0 A262 CH₂═CHCH₂ H CH₃ CF₃CF₂CF₂ 0 A263 CH₃SO₂N(CH₃) H CH₃ CF₃CF₂CF₂ 0 A264 (CH₃)₂N H CH₃ CF₃CF₂CF₂ 0 A265 (CH₃)₂NSO₂ H CH₃ CF₃CF₂CF₂ 0 A266 ClCH₂ H CH₃ CF₃CF₂CF₂ 0 A267 CH₃SCH₂ H CH₃ CF₃CF₂CF₂ 0 A268 CH₃SOCH₂ H CH₃ CF₃CF₂CF₂ 0 A269 CH₃SO₂CH₂ H CH₃ CF₃CF₂CF₂ 0 A270 H H CH₃ CF₂Cl 0 A271 CH₃ H CH₃ CF₂Cl 0 A272 CH₃CH₂ H CH₃ CF₂Cl 0 A273 cyclopropyl H CH₃ CF₂Cl 0 A274 (CH₃)₃C H CH₃ CF₂Cl 0 A275 (CH₃)₂CH H CH₃ CF₂Cl 0 A276 CH₃(CH₂)₂ H CH₃ CF₂Cl 0 A277 CH₃OCH₂ H CH₃ CF₂Cl 0 A278 CH₃O(CH₂)₂ H CH₃ CF₂Cl 0 A279 Ph H CH₃ CF₂Cl 0 A280 PhO H CH₃ CF₂Cl 0 A281 PhS H CH₃ CF₂Cl 0 A282 PhSO H CH₃ CF₂Cl 0 A283 PhSO₂ H CH₃ CF₂Cl 0 A284 CH₃S H CH₃ CF₂Cl 0 A285 CH₃SO H CH₃ CF₂Cl 0 A286 CF₃ H CH₃ CF₂Cl 0 A287 F₂CH H CH₃ CF₂Cl 0 A288 HCC H CH₃ CF₂Cl 0 A289 CH₃CC H CH₃ CF₂Cl 0 A290 CH₂═CH H CH₃ CF₂Cl 0 A291 CH₂═CHCH₂ H CH₃ CF₂Cl 0 A292 CH₃SO₂N(CH₃) H CH₃ CF₂Cl 0 A293 (CH₃)₂N H CH₃ CF₂Cl 0 A294 (CH₃)₂NSO₂ H CH₃ CF₂Cl 0 A295 ClCH₂ H CH₃ CF₂Cl 0 A296 CH₃SCH₂ H CH₃ CF₂Cl 0 A297 CH₃SOCH₂ H CH₃ CF₂Cl 0 A298 CH₃SO₂CH₂ H CH₃ CF₂Cl 0 A299 H H CH₃ CHF₂ 0 A300 CH₃ H CH₃ CHF₂ 0 A301 CH₃CH₂ H CH₃ CHF₂ 0 A302 cyclopropyl H CH₃ CHF₂ 0 A303 (CH₃)₃C H CH₃ CHF₂ 0 A304 (CH₃)₂CH H CH₃ CHF₂ 0 A305 CH₃(CH₂)₂ H CH₃ CHF₂ 0 A306 CH₃OCH₂ H CH₃ CHF₂ 0 A307 CH₃O(CH₂)₂ H CH₃ CHF₂ 0 A308 Ph H CH₃ CHF₂ 0 A309 PhO H CH₃ CHF₂ 0 A310 PhS H CH₃ CHF₂ 0 A311 PhSO H CH₃ CHF₂ 0 A312 PhSO₂ H CH₃ CHF₂ 0 A313 CH₃S H CH₃ CHF₂ 0 A314 CH₃SO H CH₃ CHF₂ 0 A315 CF₃ H CH₃ CHF₂ 0 A316 F₂CH H CH₃ CHF₂ 0 A317 HCC H CH₃ CHF₂ 0 A318 CH₃CC H CH₃ CHF₂ 0 A319 CH₂═CH H CH₃ CHF₂ 0 A320 CH₂═CHCH₂ H CH₃ CHF₂ 0 A321 CH₃SO₂N(CH₃) H CH₃ CHF₂ 0 A322 (CH₃)₂N H CH₃ CHF₂ 0 A323 (CH₃)₂NSO₂ H CH₃ CHF₂ 0 A324 ClCH₂ H CH₃ CHF₂ 0 A325 CH₃SCH₂ H CH₃ CHF₂ 0 A326 CH₃SOCH₂ H CH₃ CHF₂ 0 A327 CH₃SO₂CH₂ H CH₃ CHF₂ 0 A328 H H CH₃ CCl₃ 0 A329 CH₃ H CH₃ CCl₃ 0 A330 CH₃CH₂ H CH₃ CCl₃ 0 A331 cyclopropyl H CH₃ CCl₃ 0 A332 (CH₃)₃C H CH₃ CCl₃ 0 A333 (CH₃)₂CH H CH₃ CCl₃ 0 A334 CH₃(CH₂)₂ H CH₃ CCl₃ 0 A335 CH₃OCH₂ H CH₃ CCl₃ 0 A336 CH₃O(CH₂)₂ H CH₃ CCl₃ 0 A337 Ph H CH₃ CCl₃ 0 A338 PhO H CH₃ CCl₃ 0 A339 PhS H CH₃ CCl₃ 0 A340 PhSO H CH₃ CCl₃ 0 A341 PhSO₂ H CH₃ CCl₃ 0 A342 CH₃S H CH₃ CCl₃ 0 A343 CH₃SO H CH₃ CCl₃ 0 A344 CF₃ H CH₃ CCl₃ 0 A345 F₂CH H CH₃ CCl₃ 0 A346 HCC H CH₃ CCl₃ 0 A347 CH₃CC H CH₃ CCl₃ 0 A348 CH₂═CH H CH₃ CCl₃ 0 A349 CH₂═CHCH₂ H CH₃ CCl₃ 0 A350 CH₃SO₂N(CH₃) H CH₃ CCl₃ 0 A351 (CH₃)₂N H CH₃ CCl₃ 0 A352 (CH₃)₂NSO₂ H CH₃ CCl₃ 0 A353 ClCH₂ H CH₃ CCl₃ 0 A354 CH₃SCH₂ H CH₃ CCl₃ 0 A355 CH₃SOCH₂ H CH₃ CCl₃ 0 A356 CH₃SO₂CH₂ H CH₃ CCl₃ 0 A357 H H Ph CF₃ 0 A358 CH₃ H Ph CF₃ 0 A359 CH₃CH₂ H Ph CF₃ 0 A360 cyclopropyl H Ph CF₃ 0 A361 (CH₃)₃C H Ph CF₃ 0 A362 (CH₃)₂CH H Ph CF₃ 0 A363 CH₃(CH₂)₂ H Ph CF₃ 0 A364 CH₃OCH₂ H Ph CF₃ 0 A365 CH₃O(CH₂)₂ H Ph CF₃ 0 A366 Ph H Ph CF₃ 0 A367 PhO H Ph CF₃ 0 A368 PhS H Ph CF₃ 0 A369 PhSO H Ph CF₃ 0 A370 PhSO₂ H Ph CF₃ 0 A371 CH₃S H Ph CF₃ 0 A372 CH₃SO H Ph CF₃ 0 A373 CF₃ H Ph CF₃ 0 A374 F₂CH H Ph CF₃ 0 A375 HCC H Ph CF₃ 0 A376 CH₃CC H Ph CF₃ 0 A377 CH₂═CH H Ph CF₃ 0 A378 CH₂═CHCH₂ H Ph CF₃ 0 A379 CH₃SO₂N(CH₃) H Ph CF₃ 0 A380 (CH₃)₂N H Ph CF₃ 0 A381 (CH₃)₂NSO₂ H Ph CF₃ 0 A382 ClCH₂ H Ph CF₃ 0 A383 CH₃SCH₂ H Ph CF₃ 0 A384 CH₃SOCH₂ H Ph CF₃ 0 A385 CH₃SO₂CH₂ H Ph CF₃ 0 A386 H H Ph CF₃CF₂ 0 A387 CH₃ H Ph CF₃CF₂ 0 A388 CH₃CH₂ H Ph CF₃CF₂ 0 A389 cyclopropyl H Ph CF₃CF₂ 0 A390 (CH₃)₃C H Ph CF₃CF₂ 0 A391 (CH₃)₂CH H Ph CF₃CF₂ 0 A392 CH₃(CH₂)₂ H Ph CF₃CF₂ 0 A393 CH₃OCH₂ H Ph CF₃CF₂ 0 A394 CH₃O(CH₂)₂ H Ph CF₃CF₂ 0 A395 Ph H Ph CF₃CF₂ 0 A396 PhO H Ph CF₃CF₂ 0 A397 PhS H Ph CF₃CF₂ 0 A398 PhSO H Ph CF₃CF₂ 0 A399 PhSO₂ H Ph CF₃CF₂ 0 A400 CH₃S H Ph CF₃CF₂ 0 A401 CH₃SO H Ph CF₃CF₂ 0 A402 CF₃ H Ph CF₃CF₂ 0 A403 F₂CH H Ph CF₃CF₂ 0 A404 HCC H Ph CF₃CF₂ 0 A405 CH₃CC H Ph CF₃CF₂ 0 A406 CH₂═CH H Ph CF₃CF₂ 0 A407 CH₂═CHCH₂ H Ph CF₃CF₂ 0 A408 CH₃SO₂N(CH₃) H Ph CF₃CF₂ 0 A409 (CH₃)₂N H Ph CF₃CF₂ 0 A410 (CH₃)₂NSO₂ H Ph CF₃CF₂ 0 A411 ClCH₂ H Ph CF₃CF₂ 0 A412 CH₃SCH₂ H Ph CF₃CF₂ 0 A413 CH₃SOCH₂ H Ph CF₃CF₂ 0 A414 CH₃SO₂CH₂ H Ph CF₃CF₂ 0 A415 H H Ph CF₃CF₂CF₂ 0 A416 CH₃ H Ph CF₃CF₂CF₂ 0 A417 CH₃CH₂ H Ph CF₃CF₂CF₂ 0 A418 cyclopropyl H Ph CF₃CF₂CF₂ 0 A419 (CH₃)₃C H Ph CF₃CF₂CF₂ 0 A420 (CH₃)₂CH H Ph CF₃CF₂CF₂ 0 A421 CH₃(CH₂)₂ H Ph CF₃CF₂CF₂ 0 A422 CH₃OCH₂ H Ph CF₃CF₂CF₂ 0 A423 CH₃O(CH₂)₂ H Ph CF₃CF₂CF₂ 0 A424 Ph H Ph CF₃CF₂CF₂ 0 A425 PhO H Ph CF₃CF₂CF₂ 0 A426 PhS H Ph CF₃CF₂CF₂ 0 A427 PhSO H Ph CF₃CF₂CF₂ 0 A428 PhSO₂ H Ph CF₃CF₂CF₂ 0 A429 CH₃S H Ph CF₃CF₂CF₂ 0 A430 CH₃SO H Ph CF₃CF₂CF₂ 0 A431 CF₃ H Ph CF₃CF₂CF₂ 0 A432 F₂CH H Ph CF₃CF₂CF₂ 0 A433 HCC H Ph CF₃CF₂CF₂ 0 A434 CH₃CC H Ph CF₃CF₂CF₂ 0 A435 CH₂═CH H Ph CF₃CF₂CF₂ 0 A436 CH₂═CHCH₂ H Ph CF₃CF₂CF₂ 0 A437 CH₃SO₂N(CH₃) H Ph CF₃CF₂CF₂ 0 A438 (CH₃)₂N H Ph CF₃CF₂CF₂ 0 A439 (CH₃)₂NSO₂ H Ph CF₃CF₂CF₂ 0 A440 ClCH₂ H Ph CF₃CF₂CF₂ 0 A441 CH₃SCH₂ H Ph CF₃CF₂CF₂ 0 A442 CH₃SOCH₂ H Ph CF₃CF₂CF₂ 0 A443 CH₃SO₂CH₂ H Ph CF₃CF₂CF₂ 0 A444 H H Ph CF₂Cl 0 A445 CH₃ H Ph CF₂Cl 0 A446 CH₃CH₂ H Ph CF₂Cl 0 A447 cyclopropyl H Ph CF₂Cl 0 A448 (CH₃)₃C H Ph CF₂Cl 0 A449 (CH₃)₂CH H Ph CF₂Cl 0 A450 CH₃(CH₂)₂ H Ph CF₂Cl 0 A451 CH₃OCH₂ H Ph CF₂Cl 0 A452 CH₃O(CH₂)₂ H Ph CF₂Cl 0 A453 Ph H Ph CF₂Cl 0 A454 PhO H Ph CF₂Cl 0 A455 PhS H Ph CF₂Cl 0 A456 PhSO H Ph CF₂Cl 0 A457 PhSO₂ H Ph CF₂Cl 0 A458 CH₃S H Ph CF₂Cl 0 A459 CH₃SO H Ph CF₂Cl 0 A460 CF₃ H Ph CF₂Cl 0 A461 F₂CH H Ph CF₂Cl 0 A462 HCC H Ph CF₂Cl 0 A463 CH₃CC H Ph CF₂Cl 0 A464 CH₂═CH H Ph CF₂Cl 0 A465 CH₂═CHCH₂ H Ph CF₂Cl 0 A466 CH₃SO₂N(CH₃) H Ph CF₂Cl 0 A467 (CH₃)₂N H Ph CF₂Cl 0 A468 (CH₃)₂NSO₂ H Ph CF₂Cl 0 A469 ClCH₂ H Ph CF₂Cl 0 A470 CH₃SCH₂ H Ph CF₂Cl 0 A471 CH₃SOCH₂ H Ph CF₂Cl 0 A472 CH₃SO₂CH₂ H Ph CF₂Cl 0 A473 H H Ph CHF₂ 0 A474 CH₃ H Ph CHF₂ 0 A475 CH₃CH₂ H Ph CHF₂ 0 A476 cyclopropyl H Ph CHF₂ 0 A477 (CH₃)₃C H Ph CHF₂ 0 A478 (CH₃)₂CH H Ph CHF₂ 0 A479 CH₃(CH₂)₂ H Ph CHF₂ 0 A480 CH₃OCH₂ H Ph CHF₂ 0 A481 CH₃O(CH₂)₂ H Ph CHF₂ 0 A482 Ph H Ph CHF₂ 0 A483 PhO H Ph CHF₂ 0 A484 PhS H Ph CHF₂ 0 A485 PhSO H Ph CHF₂ 0 A486 PhSO₂ H Ph CHF₂ 0 A487 CH₃S H Ph CHF₂ 0 A488 CH₃SO H Ph CHF₂ 0 A489 CF₃ H Ph CHF₂ 0 A490 F₂CH H Ph CHF₂ 0 A491 HCC H Ph CHF₂ 0 A492 CH₃CC H Ph CHF₂ 0 A493 CH₂═CH H Ph CHF₂ 0 A494 CH₂═CHCH₂ H Ph CHF₂ 0 A495 CH₃SO₂N(CH₃) H Ph CHF₂ 0 A496 (CH₃)₂N H Ph CHF₂ 0 A497 (CH₃)₂NSO₂ H Ph CHF₂ 0 A498 ClCH₂ H Ph CHF₂ 0 A499 CH₃SCH₂ H Ph CHF₂ 0 A500 CH₃SOCH₂ H Ph CHF₂ 0 A501 CH₃SO₂CH₂ H Ph CHF₂ 0 A502 H H Ph CCl₃ 0 A503 CH₃ H Ph CCl₃ 0 A504 CH₃CH₂ H Ph CCl₃ 0 A505 cyclopropyl H Ph CCl₃ 0 A506 (CH₃)₃C H Ph CCl₃ 0 A507 (CH₃)₂CH H Ph CCl₃ 0 A508 CH₃(CH₂)₂ H Ph CCl₃ 0 A509 CH₃OCH₂ H Ph CCl₃ 0 A510 CH₃O(CH₂)₂ H Ph CCl₃ 0 A511 Ph H Ph CCl₃ 0 A512 PhO H Ph CCl₃ 0 A513 PhS H Ph CCl₃ 0 A514 PhSO H Ph CCl₃ 0 A515 PhSO₂ H Ph CCl₃ 0 A516 CH₃S H Ph CCl₃ 0 A517 CH₃SO H Ph CCl₃ 0 A518 CF₃ H Ph CCl₃ 0 A519 F₂CH H Ph CCl₃ 0 A520 HCC H Ph CCl₃ 0 A521 CH₃CC H Ph CCl₃ 0 A522 CH₂═CH H Ph CCl₃ 0 A523 CH₂═CHCH₂ H Ph CCl₃ 0 A524 CH₃SO₂N(CH₃) H Ph CCl₃ 0 A525 (CH₃)₂N H Ph CCl₃ 0 A526 (CH₃)₂NSO₂ H Ph CCl₃ 0 A527 ClCH₂ H Ph CCl₃ 0 A528 CH₃SCH₂ H Ph CCl₃ 0 A529 CH₃SOCH₂ H Ph CCl₃ 0 A530 CH₃SO₂CH₂ H Ph CCl₃ 0 A531 H CH₃ H CF₃ 0 A532 H CH₃CH₂ H CF₃ 0 A533 H cyclopropyl H CF₃ 0 A534 H (CH₃)₃CH H CF₃ 0 A535 H (CH₃)₂CH H CF₃ 0 A536 H CH₃(CH₂)₂ H CF₃ 0 A537 H CH₃OCH₂ H CF₃ 0 A538 H CH₃O(CH₂)₂ H CF₃ 0 A539 H Ph H CF₃ 0 A540 H PhO H CF₃ 0 A541 H PhS H CF₃ 0 A542 H PhSO H CF₃ 0 A543 H PhSO₂ H CF₃ 0 A544 H CH₃S H CF₃ 0 A545 H CH₃SO H CF₃ 0 A546 H CF₃ H CF₃ 0 A547 H F₂CH H CF₃ 0 A548 H HCC H CF₃ 0 A549 H CH₃CC H CF₃ 0 A550 H CH₂═CH H CF₃ 0 A551 H CH₂═CHCH₂ H CF₃ 0 A552 H CH₃SO₂N(CH₃) H CF₃ 0 A553 H (CH₃)₂N H CF₃ 0 A554 H (CH₃)₂NSO₂ H CF₃ 0 A555 H CH₃SCH₂ H CF₃ 0 A556 H CH₃SOCH₂ H CF₃ 0 A557 H CH₃SO₂CH₂ H CF₃ 0 A558 H CH₃ H CF₃CF₂ 0 A559 H CH₃CH₂ H CF₃CF₂ 0 A560 H cyclopropyl H CF₃CF₂ 0 A561 H (CH₃)₃C H CF₃CF₂ 0 A562 H (CH₃)₂CH H CF₃CF₂ 0 A563 H CH₃(CH₂)₂ H CF₃CF₂ 0 A564 H CH₃OCH₂ H CF₃CF₂ 0 A565 H CH₃O(CH₂)₂ H CF₃CF₂ 0 A566 H Ph H CF₃CF₂ 0 A567 H PhO H CF₃CF₂ 0 A568 H PhS H CF₃CF₂ 0 A569 H PhSO H CF₃CF₂ 0 A570 H PhSO₂ H CF₃CF₂ 0 A571 H CH₃S H CF₃CF₂ 0 A572 H CH₃SO H CF₃CF₂ 0 A573 H CF₃ H CF₃CF₂ 0 A574 H F₂CH H CF₃CF₂ 0 A575 H HCC H CF₃CF₂ 0 A576 H CH₃CC H CF₃CF₂ 0 A577 H CH₂═CH H CF₃CF₂ 0 A578 H CH₂═CHCH₂ H CF₃CF₂ 0 A579 H CH₃SO₂N(CH₃) H CF₃CF₂ 0 A580 H (CH₃)₂N H CF₃CF₂ 0 A581 H (CH₃)₂NSO₂ H CF₃CF₂ 0 A582 H CH₃SCH₂ H CF₃CF₂ 0 A583 H CH₃SOCH₂ H CF₃CF₂ 0 A584 H CH₃SO₂CH₂ H CF₃CF₂ 0 A585 H CH₃ H CF₃CF₂CF₂ 0 A586 H CH₃CH₂ H CF₃CF₂CF₂ 0 A587 H cyclopropyl H CF₃CF₂CF₂ 0 A588 H (CH₃)₃C H CF₃CF₂CF₂ 0 A589 H (CH₃)₂CH H CF₃CF₂CF₂ 0 A590 H CH₃(CH₂)₂ H CF₃CF₂CF₂ 0 A591 H CH₃OCH₂ H CF₃CF₂CF₂ 0 A592 H CH₃O(CH₂)₂ H CF₃CF₂CF₂ 0 A593 H Ph H CF₃CF₂CF₂ 0 A594 H PhO H CF₃CF₂CF₂ 0 A595 H PhS H CF₃CF₂CF₂ 0 A596 H PhSO H CF₃CF₂CF₂ 0 A597 H PhSO₂ H CF₃CF₂CF₂ 0 A598 H CH₃S H CF₃CF₂CF₂ 0 A599 H CH₃SO H CF₃CF₂CF₂ 0 A600 H CF₃ H CF₃CF₂CF₂ 0 A601 H F₂CH H CF₃CF₂CF₂ 0 A602 H HCC H CF₃CF₂CF₂ 0 A603 H CH₃CC H CF₃CF₂CF₂ 0 A604 H CH₂═CH H CF₃CF₂CF₂ 0 A605 H CH₂═CHCH₂ H CF₃CF₂CF₂ 0 A606 H CH₃SO₂N(CH₃) H CF₃CF₂CF₂ 0 A607 H (CH₃)₂N H CF₃CF₂CF₂ 0 A608 H (CH₃)₂NSO₂ H CF₃CF₂CF₂ 0 A609 H CH₃SCH₂ H CF₃CF₂CF₂ 0 A610 H CH₃SOCH₂ H CF₃CF₂CF₂ 0 A611 H CH₃SO₂CH₂ H CF₃CF₂CF₂ 0 A612 H CH₃ H CF₂Cl 0 A613 H CH₃CH₂ H CF₂Cl 0 A614 H cyclopropyl H CF₂Cl 0 A615 H (CH₃)₃C H CF₂Cl 0 A616 H (CH₃)₂CH H CF₂Cl 0 A617 H CH₃(CH₂)₂ H CF₂Cl 0 A618 H CH₃OCH₂ H CF₂Cl 0 A619 H CH₃O(CH₂)₂ H CF₂Cl 0 A620 H Ph H CF₂Cl 0 A621 H PhO H CF₂Cl 0 A622 H PhS H CF₂Cl 0 A623 H PhSO H CF₂Cl 0 A624 H PhSO₂ H CF₂Cl 0 A625 H CH₃S H CF₂Cl 0 A626 H CH₃SO H CF₂Cl 0 A627 H CF₃ H CF₂Cl 0 A628 H F₂CH H CF₂Cl 0 A629 H HCC H CF₂Cl 0 A630 H CH₃CC H CF₂Cl 0 A631 H CH₂═CH H CF₂Cl 0 A632 H CH₂═CHCH₂ H CF₂Cl 0 A633 H CH₃SO₂N(CH₃) H CF₂Cl 0 A634 H (CH₃)₂N H CF₂Cl 0 A635 H (CH₃)₂NSO₂ H CF₂Cl 0 A636 H CH₃SCH₂ H CF₂Cl 0 A637 H CH₃SOCH₂ H CF₂Cl 0 A638 H CH₃SO₂CH₂ H CF₂Cl 0 A639 H CH₃ H CHF₂ 0 A640 H CH₃CH₂ H CHF₂ 0 A641 H cyclopropyl H CHF₂ 0 A642 H (CH₃)₃C H CHF₂ 0 A643 H (CH₃)₂CH H CHF₂ 0 A644 H CH₃(CH₂)₂ H CHF₂ 0 A645 H CH₃OCH₂ H CHF₂ 0 A646 H CH₃O(CH₂)₂ H CHF₂ 0 A647 H Ph H CHF₂ 0 A648 H PhO H CHF₂ 0 A649 H PhS H CHF₂ 0 A650 H PhSO H CHF₂ 0 A651 H PhSO₂ H CHF₂ 0 A652 H CH₃S H CHF₂ 0 A653 H CH₃SO H CHF₂ 0 A654 H CF₃ H CHF₂ 0 A655 H F₂CH H CHF₂ 0 A656 H HCC H CHF₂ 0 A657 H CH₃CC H CHF₂ 0 A658 H CH₂═CH H CHF₂ 0 A659 H CH₂═CHCH₂ H CHF₂ 0 A660 H CH₃SO₂N(CH₃) H CHF₂ 0 A661 H (CH₃)₂N H CHF₂ 0 A662 H (CH₃)₂NSO₂ H CHF₂ 0 A663 H CH₃SCH₂ H CHF₂ 0 A664 H CH₃SOCH₂ H CHF₂ 0 A665 H CH₃SO₂CH₂ H CHF₂ 0 A666 H CH₃ H CCl₃ 0 A667 H CH₃CH₂ H CCl₃ 0 A668 H cyclopropyl H CCl₃ 0 A669 H (CH₃)₃C H CCl₃ 0 A670 H (CH₃)₂CH H CCl₃ 0 A671 H CH₃(CH₂)₂ H CCl₃ 0 A672 H CH₃OCH₂ H CCl₃ 0 A673 H CH₃O(CH₂)₂ H CCl₃ 0 A674 H Ph H CCl₃ 0 A675 H PhO H CCl₃ 0 A676 H PhS H CCl₃ 0 A677 H PhSO H CCl₃ 0 A678 H PhSO₂ H CCl₃ 0 A679 H CH₃S H CCl₃ 0 A680 H CH₃SO H CCl₃ 0 A681 H CF₃ H CCl₃ 0 A682 H F₂CH H CCl₃ 0 A683 H HCC H CCl₃ 0 A684 H CH₃CC H CCl₃ 0 A685 H CH₂═CH H CCl₃ 0 A686 H CH₂═CHCH₂ H CCl₃ 0 A687 H CH₃SO₂N(CH₃) H CCl₃ 0 A688 H (CH₃)₂N H CCl₃ 0 A689 H (CH₃)₂NSO₂ H CCl₃ 0 A690 H CH₃SCH₂ H CCl₃ 0 A691 H CH₃SOCH₂ H CCl₃ 0 A692 H CH₃SO₂CH₂ H CCl₃ 0 A693 H CH₃ CH₃ CF₃ 0 A694 H CH₃CH₂ CH₃ CF₃ 0 A695 H cyclopropyl CH₃ CF₃ 0 A696 H (CH₃)₃C CH₃ CF₃ 0 A697 H (CH₃)₂CH CH₃ CF₃ 0 A698 H CH₃(CH₂)₂ CH₃ CF₃ 0 A699 H CH₃OCH₂ CH₃ CF₃ 0 A700 H CH₃O(CH₂)₂ CH₃ CF₃ 0 A701 H Ph CH₃ CF₃ 0 A702 H PhO CH₃ CF₃ 0 A703 H PhS CH₃ CF₃ 0 A704 H PhSO CH₃ CF₃ 0 A705 H PhSO₂ CH₃ CF₃ 0 A706 H CH₃S CH₃ CF₃ 0 A707 H CH₃SO CH₃ CF₃ 0 A708 H CF₃ CH₃ CF₃ 0 A709 H F₂CH CH₃ CF₃ 0 A710 H HCC CH₃ CF₃ 0 A711 H CH₃CC CH₃ CF₃ 0 A712 H CH₂═CH CH₃ CF₃ 0 A713 H CH₂═CHCH₂ CH₃ CF₃ 0 A714 H CH₃SO₂N(CH₃) CH₃ CF₃ 0 A715 H (CH₃)₂N CH₃ CF₃ 0 A716 H (CH₃)₂NSO₂ CH₃ CF₃ 0 A717 H CH₃SCH₂ CH₃ CF₃ 0 A718 H CH₃SOCH₂ CH₃ CF₃ 0 A719 H CH₃SO₂CH₂ CH₃ CF₃ 0 A720 H CH₃ CH₃ CF₃CF₂ 0 A721 H CH₃CH₂ CH₃ CF₃CF₂ 0 A722 H cyclopropyl CH₃ CF₃CF₂ 0 A723 H (CH₃)₃C CH₃ CF₃CF₂ 0 A724 H (CH₃)₂CH CH₃ CF₃CF₂ 0 A725 H CH₃(CH₂)₂ CH₃ CF₃CF₂ 0 A726 H CH₃OCH₂ CH₃ CF₃CF₂ 0 A727 H CH₃O(CH₂)₂ CH₃ CF₃CF₂ 0 A728 H Ph CH₃ CF₃CF₂ 0 A729 H PhO CH₃ CF₃CF₂ 0 A730 H PhS CH₃ CF₃CF₂ 0 A731 H PhSO CH₃ CF₃CF₂ 0 A732 H PhSO₂ CH₃ CF₃CF₂ 0 A733 H CH₃S CH₃ CF₃CF₂ 0 A734 H CH₃SO CH₃ CF₃CF₂ 0 A735 H CF₃ CH₃ CF₃CF₂ 0 A736 H F₂CH CH₃ CF₃CF₂ 0 A737 H HCC CH₃ CF₃CF₂ 0 A738 H CH₃CC CH₃ CF₃CF₂ 0 A739 H CH₂═CH CH₃ CF₃CF₂ 0 A740 H CH₂═CHCH₂ CH₃ CF₃CF₂ 0 A741 H CH₃SO₂N(CH₃) CH₃ CF₃CF₂ 0 A742 H (CH₃)₂N CH₃ CF₃CF₂ 0 A743 H (CH₃)₂NSO₂ CH₃ CF₃CF₂ 0 A744 H CH₃SCH₂ CH₃ CF₃CF₂ 0 A745 H CH₃SOCH₂ CH₃ CF₃CF₂ 0 A746 H CH₃SO₂CH₂ CH₃ CF₃CF₂ 0 A747 H CH₃ CH₃ CF₃CF₂CF₂ 0 A748 H CH₃CH₂ CH₃ CF₃CF₂CF₂ 0 A749 H cyclopropyl CH₃ CF₃CF₂CF₂ 0 A750 H (CH₃)₃C CH₃ CF₃CF₂CF₂ 0 A751 H (CH₃)₂CH CH₃ CF₃CF₂CF₂ 0 A752 H CH₃(CH₂)₂ CH₃ CF₃CF₂CF₂ 0 A753 H CH₃OCH₂ CH₃ CF₃CF₂CF₂ 0 A754 H CH₃O(CH₂)₂ CH₃ CF₃CF₂CF₂ 0 A755 H Ph CH₃ CF₃CF₂CF₂ 0 A756 H PhO CH₃ CF₃CF₂CF₂ 0 A757 H PhS CH₃ CF₃CF₂CF₂ 0 A758 H PhSO CH₃ CF₃CF₂CF₂ 0 A759 H PhSO₂ CH₃ CF₃CF₂CF₂ 0 A760 H CH₃S CH₃ CF₃CF₂CF₂ 0 A761 H CH₃SO CH₃ CF₃CF₂CF₂ 0 A762 H CF₃ CH₃ CF₃CF₂CF₂ 0 A763 H F₂CH CH₃ CF₃CF₂CF₂ 0 A764 H HCC CH₃ CF₃CF₂CF₂ 0 A765 H CH₃CC CH₃ CF₃CF₂CF₂ 0 A766 H CH₂═CH CH₃ CF₃CF₂CF₂ 0 A767 H CH₂═CHCH₂ CH₃ CF₃CF₂CF₂ 0 A768 H CH₃SO₂N(CH₃) CH₃ CF₃CF₂CF₂ 0 A769 H (CH₃)₂N CH₃ CF₃CF₂CF₂ 0 A770 H (CH₃)₂NSO₂ CH₃ CF₃CF₂CF₂ 0 A771 H CH₃SCH₂ CH₃ CF₃CF₂CF₂ 0 A772 H CH₃SOCH₂ CH₃ CF₃CF₂CF₂ 0 A773 H CH₃SO₂CH₂ CH₃ CF₃CF₂CF₂ 0 A774 H CH₃ CH₃ CF₂Cl 0 A775 H CH₃CH₂ CH₃ CF₂Cl 0 A776 H cyclopropyl CH₃ CF₂Cl 0 A777 H (CH₃)₃C CH₃ CF₂Cl 0 A778 H (CH₃)₂CH CH₃ CF₂Cl 0 A779 H CH₃(CH₂)₂ CH₃ CF₂Cl 0 A780 H CH₃OCH₂ CH₃ CF₂Cl 0 A781 H CH₃O(CH₂)₂ CH₃ CF₂Cl 0 A782 H Ph CH₃ CF₂Cl 0 A783 H PhO CH₃ CF₂Cl 0 A784 H PhS CH₃ CF₂Cl 0 A785 H PhSO CH₃ CF₂Cl 0 A786 H PhSO₂ CH₃ CF₂Cl 0 A787 H CH₃S CH₃ CF₂Cl 0 A788 H CH₃SO CH₃ CF₂Cl 0 A789 H CF₃ CH₃ CF₂Cl 0 A790 H F₂CH CH₃ CF₂Cl 0 A791 H HCC CH₃ CF₂Cl 0 A792 H CH₃CC CH₃ CF₂Cl 0 A793 H CH₂═CH CH₃ CF₂Cl 0 A794 H CH₂═CHCH₂ CH₃ CF₂Cl 0 A795 H CH₃SO₂N(CH₃) CH₃ CF₂Cl 0 A796 H (CH₃)₂N CH₃ CF₂Cl 0 A797 H (CH₃)₂NSO₂ CH₃ CF₂Cl 0 A798 H CH₃SCH₂ CH₃ CF₂Cl 0 A799 H CH₃SOCH₂ CH₃ CF₂Cl 0 A800 H CH₃SO₂CH₂ CH₃ CF₂Cl 0 A801 H CH₃ CH₃ CHF₂ 0 A802 H CH₃CH₂ CH₃ CHF₂ 0 A803 H cyclopropyl CH₃ CHF₂ 0 A804 H (CH₃)₃C CH₃ CHF₂ 0 A805 H (CH₃)₂CH CH₃ CHF₂ 0 A806 H CH₃(CH₂)₂ CH₃ CHF₂ 0 A807 H CH₃OCH₂ CH₃ CHF₂ 0 A808 H CH₃O(CH₂)₂ CH₃ CHF₂ 0 A809 H Ph CH₃ CHF₂ 0 A810 H PhO CH₃ CHF₂ 0 A811 H PhS CH₃ CHF₂ 0 A812 H PhSO CH₃ CHF₂ 0 A813 H PhSO₂ CH₃ CHF₂ 0 A814 H CH₃S CH₃ CHF₂ 0 A815 H CH₃SO CH₃ CHF₂ 0 A816 H CF₃ CH₃ CHF₂ 0 A817 H F₂CH CH₃ CHF₂ 0 A818 H HCC CH₃ CHF₂ 0 A819 H CH₃CC CH₃ CHF₂ 0 A820 H CH₂═CH CH₃ CHF₂ 0 A821 H CH₂═CHCH₂ CH₃ CHF₂ 0 A822 H CH₃SO₂N(CH₃) CH₃ CHF₂ 0 A823 H (CH₃)₂N CH₃ CHF₂ 0 A824 H (CH₃)₂NSO₂ CH₃ CHF₂ 0 A825 H CH₃SCH₂ CH₃ CHF₂ 0 A826 H CH₃SOCH₂ CH₃ CHF₂ 0 A827 H CH₃SO₂CH₂ CH₃ CHF₂ 0 A828 H CH₃ CH₃ CCl₃ 0 A829 H CH₃CH₂ CH₃ CCl₃ 0 A830 H cyclopropyl CH₃ CCl₃ 0 A831 H (CH₃)₃C CH₃ CCl₃ 0 A832 H (CH₃)₂CH CH₃ CCl₃ 0 A833 H CH₃(CH₂)₂ CH₃ CCl₃ 0 A834 H CH₃OCH₂ CH₃ CCl₃ 0 A835 H CH₃O(CH₂)₂ CH₃ CCl₃ 0 A836 H Ph CH₃ CCl₃ 0 A837 H PhO CH₃ CCl₃ 0 A838 H PhS CH₃ CCl₃ 0 A839 H PhSO CH₃ CCl₃ 0 A840 H PhSO₂ CH₃ CCl₃ 0 A841 H CH₃S CH₃ CCl₃ 0 A842 H CH₃SO CH₃ CCl₃ 0 A843 H CF₃ CH₃ CCl₃ 0 A844 H F₂CH CH₃ CCl₃ 0 A845 H HCC CH₃ CCl₃ 0 A846 H CH₃CC CH₃ CCl₃ 0 A847 H CH₂═CH CH₃ CCl₃ 0 A848 H CH₂═CHCH₂ CH₃ CCl₃ 0 A849 H CH₃SO₂N(CH₃) CH₃ CCl₃ 0 A850 H (CH₃)₂N CH₃ CCl₃ 0 A851 H (CH₃)₂NSO₂ CH₃ CCl₃ 0 A852 H CH₃SCH₂ CH₃ CCl₃ 0 A853 H CH₃SOCH₂ CH₃ CCl₃ 0 A854 H CH₃SO₂CH₂ CH₃ CCl₃ 0 A855 H CH₃ Ph CF₃ 0 A856 H CH₃CH₂ Ph CF₃ 0 A857 H (CH₃)₂CH Ph CF₃ 0 A858 H (CH₃)₂CH Ph CF₃ 0 A859 H cyclopropyl Ph CF₃ 0 A860 H CH₃(CH₂)₂ Ph CF₃ 0 A861 H CH₃OCH₂ Ph CF₃ 0 A862 H CH₃O(CH₂)₂ Ph CF₃ 0 A863 H Ph Ph CF₃ 0 A864 H PhO Ph CF₃ 0 A865 H PhS Ph CF₃ 0 A866 H PhSO Ph CF₃ 0 A867 H PhSO₂ Ph CF₃ 0 A868 H CH₃S Ph CF₃ 0 A869 H CH₃SO Ph CF₃ 0 A870 H CF₃ Ph CF₃ 0 A871 H F₂CH Ph CF₃ 0 A872 H HCC Ph CF₃ 0 A873 H CH₃CC Ph CF₃ 0 A874 H CH₂═CH Ph CF₃ 0 A875 H CH₂═CHCH₂ Ph CF₃ 0 A876 H CH₃SO₂N(CH₃) Ph CF₃ 0 A877 H (CH₃)₂N Ph CF₃ 0 A878 H (CH₃)₂NSO₂ Ph CF₃ 0 A879 H CH₃SCH₂ Ph CF₃ 0 A880 H CH₃SOCH₂ Ph CF₃ 0 A881 H CH₃SO₂CH₂ Ph CF₃ 0 A882 H CH₃ Ph CF₃CF₂ 0 A883 H CH₃CH₂ Ph CF₃CF₂ 0 A884 H cyclopropyl Ph CF₃CF₂ 0 A885 H (CH₃)₃C Ph CF₃CF₂ 0 A886 H (CH₃)₂CH Ph CF₃CF₂ 0 A887 H CH₃(CH₂)₂ Ph CF₃CF₂ 0 A888 H CH₃OCH₂ Ph CF₃CF₂ 0 A889 H CH₃O(CH₂)₂ Ph CF₃CF₂ 0 A890 H Ph Ph CF₃CF₂ 0 A891 H PhO Ph CF₃CF₂ 0 A892 H PhS Ph CF₃CF₂ 0 A893 H PhSO Ph CF₃CF₂ 0 A894 H PhSO₂ Ph CF₃CF₂ 0 A895 H CH₃S Ph CF₃CF₂ 0 A896 H CH₃SO Ph CF₃CF₂ 0 A897 H CF₃ Ph CF₃CF₂ 0 A898 H F₂CH Ph CF₃CF₂ 0 A899 H HCC Ph CF₃CF₂ 0 A900 H CH₃CC Ph CF₃CF₂ 0 A901 H CH₂═CH Ph CF₃CF₂ 0 A902 H CH₂═CHCH₂ Ph CF₃CF₂ 0 A903 H CH₃SO₂N(CH₃) Ph CF₃CF₂ 0 A904 H (CH₃)₂N Ph CF₃CF₂ 0 A905 H (CH₃)₂NSO₂ Ph CF₃CF₂ 0 A906 H CH₃SCH₂ Ph CF₃CF₂ 0 A907 H CH₃SOCH₂ Ph CF₃CF₂ 0 A908 H CH₃SO₂CH₂ Ph CF₃CF₂ 0 A909 H CH₃ Ph CF₃CF₂CF₂ 0 A910 H CH₃CH₂ Ph CF₃CF₂CF₂ 0 A911 H cyclopropyl Ph CF₃CF₂CF₂ 0 A912 H (CH₃)₃C Ph CF₃CF₂CF₂ 0 A913 H (CH₃)₂CH Ph CF₃CF₂CF₂ 0 A914 H CH₃(CH₂)₂ Ph CF₃CF₂CF₂ 0 A915 H CH₃OCH₂ Ph CF₃CF₂CF₂ 0 A916 H CH₃O(CH₂)₂ Ph CF₃CF₂CF₂ 0 A917 H Ph Ph CF₃CF₂CF₂ 0 A918 H PhO Ph CF₃CF₂CF₂ 0 A919 H PhS Ph CF₃CF₂CF₂ 0 A920 H PhSO Ph CF₃CF₂CF₂ 0 A921 H PhSO₂ Ph CF₃CF₂CF₂ 0 A922 H CH₃S Ph CF₃CF₂CF₂ 0 A923 H CH₃SO Ph CF₃CF₂CF₂ 0 A924 H CF₃ Ph CF₃CF₂CF₂ 0 A925 H F₂CH Ph CF₃CF₂CF₂ 0 A926 H HCC Ph CF₃CF₂CF₂ 0 A927 H CH₃CC Ph CF₃CF₂CF₂ 0 A928 H CH₂═CH Ph CF₃CF₂CF₂ 0 A929 H CH₂═CHCH₂ Ph CF₃CF₂CF₂ 0 A930 H CH₃SO₂N(CH₃) Ph CF₃CF₂CF₂ 0 A931 H (CH₃)₂N Ph CF₃CF₂CF₂ 0 A932 H (CH₃)₂NSO₂ Ph CF₃CF₂CF₂ 0 A933 H CH₃SCH₂ Ph CF₃CF₂CF₂ 0 A934 H CH₃SOCH₂ Ph CF₃CF₂CF₂ 0 A935 H CH₃SO₂CH₂ Ph CF₃CF₂CF₂ 0 A936 H CH₃ Ph CF₂Cl 0 A937 H CH₃CH₂ Ph CF₂Cl 0 A938 H cyclopropyl Ph CF₂Cl 0 A939 H (CH₃)₃C Ph CF₂Cl 0 A940 H (CH₃)₂CH Ph CF₂Cl 0 A941 H CH₃(CH₂)₂ Ph CF₂Cl 0 A942 H CH₃OCH₂ Ph CF₂Cl 0 A943 H CH₃O(CH₂)₂ Ph CF₂Cl 0 A944 H Ph Ph CF₂Cl 0 A945 H PhO Ph CF₂Cl 0 A946 H PhS Ph CF₂Cl 0 A947 H PhSO Ph CF₂Cl 0 A948 H PhSO₂ Ph CF₂Cl 0 A949 H CH₃S Ph CF₂Cl 0 A950 H CH₃SO Ph CF₂Cl 0 A951 H CF₃ Ph CF₂Cl 0 A952 H F₂CH Ph CF₂Cl 0 A953 H HCC Ph CF₂Cl 0 A954 H CH₃CC Ph CF₂Cl 0 A955 H CH₂═CH Ph CF₂Cl 0 A956 H CH₂═CHCH₂ Ph CF₂Cl 0 A957 H CH₃SO₂N(CH₃) Ph CF₂Cl 0 A958 H (CH₃)₂N Ph CF₂Cl 0 A959 H (CH₃)₂NSO₂ Ph CF₂Cl 0 A960 H CH₃SCH₂ Ph CF₂Cl 0 A961 H CH₃SOCH₂ Ph CF₂Cl 0 A962 H CH₃SO₂CH₂ Ph CF₂Cl 0 A963 H CH₃ Ph CHF₂ 0 A964 H CH₃CH₂ Ph CHF₂ 0 A965 H cyclopropyl Ph CHF₂ 0 A966 H (CH₃)₃C Ph CHF₂ 0 A967 H (CH₃)₂CH Ph CHF₂ 0 A968 H CH₃(CH₂)₂ Ph CHF₂ 0 A969 H CH₃OCH₂ Ph CHF₂ 0 A970 H CH₃O(CH₂)₂ Ph CHF₂ 0 A971 H Ph Ph CHF₂ 0 A972 H PhO Ph CHF₂ 0 A973 H PhS Ph CHF₂ 0 A974 H PhSO Ph CHF₂ 0 A975 H PhSO₂ Ph CHF₂ 0 A976 H CH₃S Ph CHF₂ 0 A977 H CH₃SO Ph CHF₂ 0 A978 H CF₃ Ph CHF₂ 0 A979 H F₂CH Ph CHF₂ 0 A980 H HCC Ph CHF₂ 0 A981 H CH₃CC Ph CHF₂ 0 A982 H CH₂═CH Ph CHF₂ 0 A983 H CH₂═CHCH₂ Ph CHF₂ 0 A984 H CH₃SO₂N(CH₃) Ph CHF₂ 0 A985 H (CH₃)₂N Ph CHF₂ 0 A986 H (CH₃)₂NSO₂ Ph CHF₂ 0 A987 H CH₃SCH₂ Ph CHF₂ 0 A988 H CH₃SOCH₂ Ph CHF₂ 0 A989 H CH₃SO₂CH₂ Ph CHF₂ 0 A990 H CH₃ Ph CCl₃ 0 A991 H CH₃CH₂ Ph CCl₃ 0 A992 H cyclopropyl Ph CCl₃ 0 A993 H (CH₃)₃C Ph CCl₃ 0 A994 H (CH₃)₂CH Ph CCl₃ 0 A995 H CH₃(CH₂)₂ Ph CCl₃ 0 A996 H CH₃OCH₂ Ph CCl₃ 0 A997 H CH₃O(CH₂)₂ Ph CCl₃ 0 A998 H Ph Ph CCl₃ 0 A999 H PhO Ph CCl₃ 0  A1000 H PhS Ph CCl₃ 0  A1001 H PhSO Ph CCl₃ 0  A1002 H PhSO₂ Ph CCl₃ 0  A1003 H CH₃S Ph CCl₃ 0  A1004 H CH₃SO Ph CCl₃ 0  A1005 H CF₃ Ph CCl₃ 0  A1006 H F₂CH Ph CCl₃ 0  A1007 H HCC Ph CCl₃ 0  A1008 H CH₃CC Ph CCl₃ 0  A1009 H CH₂═CH Ph CCl₃ 0  A1010 H CH₂═CHCH₂ Ph CCl₃ 0  A1011 H CH₃SO₂N(CH₃) Ph CCl₃ 0  A1012 H (CH₃)₂N Ph CCl₃ 0  A1013 H (CH₃)₂NSO₂ Ph CCl₃ 0  A1014 H CH₃SCH₂ Ph CCl₃ 0  A1015 H CH₃SOCH₂ Ph CCl₃ 0  A1016 H CH₃SO₂CH₂ Ph CCl₃ 0  A1017 F H H CF₃ 0  A1018 Cl H H CF₃ 0  A1019 Br H H CF₃ 0  A1020 NC H H CF₃ 0  A1021 CH₃SO₂O H H CF₃ 0  A1022 CH₃O H H CF₃ 0  A1023 CH₃CH₂O H H CF₃ 0  A1024 CH₂CH═CH₂O H H CF₃ 0  A1025 HCCCH₂O H H CF₃ 0  A1026 PhCH₂S H H CF₃ 0  A1027 PhCH₂SO₂ H H CF₃ 0  A1028 ClCH₂CH₂ H H CF₃ 0  A1029 BrCH₂ H H CF₃ 0  A1030 FCH₂ H H CF₃ 0  A1031 CHF₂CH₂ H H CF₃ 0  A1032 CF₃CH₂ H H CF₃ 0  A1033 [1,3]-imidazol-1-ylmethyl H H CF₃ 0  A1034 CHCl₂CH₂ H H CF₃ 0  A1035 ClCH═CH H H CF₃ 0  A1036 Cl₂C═CH H H CF₃ 0  A1037 CF₃CH═CH H H CF₃ 0  A1038 ClCC H H CF₃ 0  A1039 PhCH₂ H H CF₃ 0  A1040 CH₃CH₂ CH₃ H CF₃ 0  A1041 CH₃ OH H CF₃ 0  A1042 CH₃ F H CF₃ 0  A1043 CH₃ Cl H CF₃ 0  A1044 F CH₃ H CF₃ 0  A1045 Cl CH₃ H CF₃ 0  A1046 H F H CF₃ 0  A1047 H Cl H CF₃ 0  A1048 H Br H CF₃ 0  A1049 H OH H CF₃ 0  A1050 H OCH₃ H CF₃ 0  A1051 H OCHF₂ H CF₃ 0  A1052 H OSO₂CH₃ H CF₃ 0  A1053 H OSO₂CF₃ H CF₃ 0  A1054 H ClCH₂ H CF₃ 0  A1055 H BrCH₂ H CF₃ 0  A1056 H FCH₂ H CF₃ 0  A1057 H CHF₂CH₂ H CF₃ 0  A1058 H CF₃CH₂ H CF₃ 0  A1059 H triazolylmethyl H CF₃ 0  A1060 H CHCl₂CH₂ H CF₃ 0  A1061 H ClCH═CH H CF₃ 0  A1062 H Cl₂C═CH H CF₃ 0  A1063 H CF₃CH═CH H CF₃ 0  A1064 H ClCC H CF₃ 0  A1065 H CH₃C(O) H CF₃ 0  A1066 H Ph H CF₃ 0  A1067 H SO₂CH₃ H CF₃ 0  A1068 H SO₂CF₃ H CF₃ 0  A1069 H NC H CF₃ 0  A1070 H NO₂ H CF₃ 0  A1071 CH₃ H F CF₃ 0  A1072 CH₃ H Cl CF₃ 0  A1073 CH₃ H Br CF₃ 0  A1074 CH₃ H NC CF₃ 0  A1075 CH₃ H CH₃O CF₃ 0  A1076 CH₃ H CH₃S CF₃ 0  A1077 CH₃ H CH₃SO CF₃ 0  A1078 CH₃ H CH₂SO₂ CF₃ 0  A1079 CH₃CH₂OCH₂ H H CF₃ 0  A1080 PhOCH₂ H H CF₃ 0  A1081

H H CF₃ 0  A1082 (CH₃)₂CH₂OCH₂ H H CF₃ 0  A1083 BrCH₂CH₂ H H CF₃ 0  A1084 FCH₂CH₂ H H CF₃ 0  A1085

H H CF₃ 0  A1086

H H CF₃ 0  A1087

H H CF₃ 0  A1088

H H CF₃ 0  A1089

H H CF₃ 0  A1090

H H CF₃ 0  A1091 cyclopropyl-CH₂ H H CF₃ 0  A1092 2,2-dichlorocycloprop-1-yl H H CF₃ 0  A1093 CH₃OC(O)CH═CH H H CF₃ 0  A1094 CH₃CH₂OC(O)CH═CH H H CF₃ 0  A1095 ClCH₂CH═CH H H CF₃ 0  A1096 CH═C═CH H H CF₃ 0  A1097 (CH₃)₂NCH₂ H H CF₃ 0  A1098 HOCH₂ H H CF₃ 0  A1099 CH₃C(O)OCH₂ H H CF₃ 0  A1100 PhC(O)OCH₂ H H CF₃ 0  A1101 PhCH₂CH₂ H H CF₃ 0  A1102 CH₃OC(O)CH₂ H H CF₃ 0  A1103 NCCH₂ H H CF₃ 0  A1104 CH₃(CH₂)₇SCH₂ H H CF₃ 0  A1105 CH₃(CH₂)₇SOCH₂ H H CF₃ 0  A1106 CH₃(CH₂)₇SO₂CH₂ H H CF₃ 0  A1107

H H CF₃ 0  A1108 ClCH₂CC H H CF₃ 0  A1109 CHF₂CH₂CH₂ H H CF₃ 0  A1110 CHCl₂CH₂CH₂ H H CF₃ 0  A1111 CF₃SO₂O H H CF₃ 0  A1112

H H CF₃ 0  A1113

H H CF₃ 0  A1114

H H CF₃ 0  A1115

H H CF₃ 0  A1116

H H CF₃ 0  A1117

H H CF₃ 0  A1118 CH₃ON═CHCH₂ H H CF₃ 0  A1119 O═CHCH₂ H H CF₃ 0  A1120 CH₃CH₂OCH₂ H H CF₂Cl 0  A1121 PhOCH₂ H H CF₂Cl 0  A1122

H H CF₂Cl 0  A1123 (CH₃)₂CH₂OCH₂ H H CF₂Cl 0  A1124 BrCH₂ H H CF₂Cl 0  A1125 FCH₂ H H CF₂Cl 0  A1126

H H CF₂Cl 0  A1127

H H CF₂Cl 0  A1128

H H CF₂Cl 0  A1129

H H CF₂Cl 0  A1130

H H CF₂Cl 0  A1131

H H CF₂Cl 0  A1132 cyclopropyl-CH₂ H H CF₂Cl 0  A1133 2,2-dichlorocycloprop-1-yl H H CF₂Cl 0  A1134 CH₃OC(O)CH═CH H H CF₂Cl 0  A1135 CH₃CH₂OC(O)CH═CH H H CF₂Cl 0  A1136 ClCH₂CH═CH H H CF₂Cl 0  A1137 CH═C═CH H H CF₂Cl 0  A1138 (CH₃)₂NCH₂ H H CF₂Cl 0  A1139 HOCH₂ H H CF₂Cl 0  A1140 CH₃C(O)OCH₂ H H CF₂Cl 0  A1141 PhC(O)OCH₂ H H CF₂Cl 0  A1142 PhCH₂ H H CF₂Cl 0  A1143 CH₃OC(O)CH₂ H H CF₂Cl 0  A1144 NCCH₂ H H CF₂Cl 0  A1145 CH₃(CH₂)₇SCH₂ H H CF₂Cl 0  A1146 CH₃(CH₂)₇SOCH₂ H H CF₂Cl 0  A1147 CH₃(CH₂)₇SO₂CH₂ H H CF₂Cl 0  A1148

H H CF₂Cl 0  A1149 ClCH₂CC H H CF₂Cl 0  A1150 Br H H CF₂Cl 0  A1151 Cl H H CF₂Cl 0  A1152 CF₃SO₂O H H CF₂Cl 0  A1153

H H CF₂Cl 0  A1154

H H CF₂Cl 0  A1155

H H CF₂Cl 0  A1156

H H CF₂Cl 0  A1157

H H CF₂Cl 0  A1158

H H CF₂Cl 0  A1159 CH₃ON═CHCH₂ H H CF₂Cl 0  A1160 O═CHCH₂ H H CF₂Cl 0  A1161 CH₃CH₂OCH₂ H H CF₂H 0  A1162 PhOCH₂ H H CF₂H 0  A1163

H H CF₂H 0  A1164 (CH₃)₂CH₂OCH₂ H H CF₂H 0  A1165 BrCH₂ H H CF₂H 0  A1166 FCH₂ H H CF₂H 0  A1167

H H CF₂H 0  A1168

H H CF₂H 0  A1169

H H CF₂H 0  A1170

H H CF₂H 0  A1171

H H CF₂H 0  A1172

H H CF₂H 0  A1173 cyclopropyl-CH₂ H H CF₂H 0  A1174 2,2-dichlorocycloprop-1-yl H H CF₂H 0  A1175 CH₃OC(O)CH═CH H H CF₂H 0  A1176 CH₃CH₂OC(O)CH═CH H H CF₂H 0  A1177 ClCH₂CH═CH H H CF₂H 0  A1178 CH═C═CH H H CF₂H 0  A1179 (CH₃)₂NCH₂ H H CF₂H 0  A1180 HOCH₂ H H CF₂H 0  A1181 CH₃C(O)OCH₂ H H CF₂H 0  A1182 PhC(O)OCH₂ H H CF₂H 0  A1183 PhCH₂ H H CF₂H 0  A1184 CH₃OC(O)CH₂ H H CF₂H 0  A1185 NCCH₂ H H CF₂H 0  A1186 CH₃(CH₂)₇SCH₂ H H CF₂H 0  A1187 CH₃(CH₂)₇SOCH₂ H H CF₂H 0  A1188 CH₃(CH₂)₇SO₂CH₂ H H CF₂H 0  A1189

H H CF₂H 0  A1190 ClCH₂CC H H CF₂H 0  A1191 Br H H CF₂H 0  A1192 Cl H H CF₂H 0  A1193 CF₃SO₂O H H CF₂H 0  A1194

H H CF₂H 0  A1195

H H CF₂H 0  A1196

H H CF₂H 0  A1197

H H CF₂H 0  A1198

H H CF₂H 0  A1199

H H CF₂H 0  A1200 CH₃ON═CHCH₂ H H CF₂H 0  A1201 O═CHCH₂ H H CF₂H 0  A1202 CH₃CH═CH H H CF₃ 0  A1203 CH₃SO₂NH H H CF₃ 0  A1204 CH₃CH₂CH₂O H CH₃ CF₃ 0  A1205 Cl CH₃ H CF₃ 0  A1206 F₂CHO H H CF₃ 0  A1207 CH₃CH₂C(O)OCH₂ H H CF₃ 0  A1208 CH₃CH₂OC(O)OCH₂ H H CF₃ 0  A1209 CH₃OCH₂OCH₂ H H CF₃ 0  A1210 CH₃ H H CF₃ 1  A1211 CH₃CH₂ H H CF₃ 1  A1212 cyclopropyl H H CF₃ 1  A1213 CH₃(CH₂)₂ H H CF₃ 1  A1214 CH₃OCH₂ H H CF₃ 1  A1215 CF₃ H H CF₃ 1  A1216 F₂CH H H CF₃ 1  A1217 ClCH₂ H H CF₃ 1  A1218 CH₃SO₂CH₂ H H CF₃ 1  A1219 CH₃ CF₃ H CH₃ 1  A1220 CH₃CH₂OCH₂ H H CF₃ 1  A1221 PhOCH₂ H H CF₃ 1  A1222 (CH₃)₂CH₂OCH₂ H H CF₃ 1  A1223 BrCH₂ H H CF₃ 1  A1224 FCH₂ H H CF₃ 1  A1225

H H CF₃ 1  A1226

H H CF₃ 1  A1227 cyclopropyl-CH₂ H H CF₃ 1  A1228 2,2-dichlorocycloprop-1-yl H H CF₃ 1  A1229 (CH₃)₂NCH₂ H H CF₃ 1  A1230 HOCH₂ H H CF₃ 1  A1231 CH₃C(O)OCH₂ H H CF₃ 1  A1232 PhC(O)OCH₂ H H CF₃ 1  A1233 PhCH₂ H H CF₃ 1  A1234 CH₃OC(O)CH₂ H H CF₃ 1  A1235 NCCH₂ H H CF₃ 1  A1236 CH₃(CH₂)₇SO₂CH₂ H H CF₃ 1  A1237 Br H H CF₃ 1  A1238 Cl H H CF₃ 1  A1239 O═CHCH₂ H H CF₃ 1  A1240 CH₃ H H CF₂Cl 1  A1241 CH₃CH₂ H H CF₂Cl 1  A1242 cyclopropyl H H CF₂Cl 1  A1243 CH₃(CH₂)₂ H H CF₂Cl 1  A1244 CH₃OCH₂ H H CF₂Cl 1  A1245 CF₃ H H CF₂Cl 1  A1246 F₂CH H H CF₂Cl 1  A1247 ClCH₂ H H CF₂Cl 1  A1248 CH₃SO₂CH₂ H H CF₂Cl 1  A1249 CH₃ CF₃ H CF₂Cl 1  A1250 CH₃CH₂OCH₂ H H CF₂Cl 1  A1251 PhOCH₂ H H CF₂Cl 1  A1252 (CH₃)₂CH₂OCH₂ H H CF₂Cl 1  A1253 BrCH₂ H H CF₂Cl 1  A1254 FCH₂ H H CF₂Cl 1  A1255

H H CF₂Cl 1  A1256

H H CF₂Cl 1  A1257 cyclopropyl-CH₂ H H CF₂Cl 1  A1258 2,2-dichlorocycloprop-1-yl H H CF₂Cl 1  A1259 (CH₃)₂NCH₂ H H CF₂Cl 1  A1260 HOCH₂ H H CF₂Cl 1  A1261 CH₃C(O)OCH₂ H H CF₂Cl 1  A1262 PhC(O)OCH₂ H H CF₂Cl 1  A1263 PhCH₂ H H CF₂Cl 1  A1264 CH₃OC(O)CH₂ H H CF₂Cl 1  A1265 NCCH₂ H H CF₂Cl 1  A1266 CH₃(CH₂)₇SO₂CH₂ H H CF₂Cl 1  A1267 Br H H CF₂Cl 1  A1268 Cl H H CF₂Cl 1  A1269 O═CHCH₂ H H CF₂Cl 1  A1270 CH₃ H H CF₂H 1  A1271 CH₃CH₂ H H CF₂H 1  A1272 cyclopropyl H H CF₂H 1  A1273 CH₃(CH₂)₂ H H CF₂H 1  A1274 CH₃OCH₂ H H CF₂H 1  A1275 CF₃ H H CF₂H 1  A1276 F₂CH H H CF₂H 1  A1277 ClCH₂ H H CF₂H 1  A1278 CH₃SO₂CH₂ H H CF₂H 1  A1279 CH₃ CF₃ H CF₂H 1  A1280 CH₃CH₂OCH₂ H H CF₂H 1  A1281 PhOCH₂ H H CF₂H 1  A1282 (CH₃)₂CH₂OCH₂ H H CF₂H 1  A1283 BrCH₂ H H CF₂H 1  A1284 FCH₂ H H CF₂H 1  A1285

H H CF₂H 1  A1286

H H CF₂H 1  A1287 cyclopropyl-CH₂ H H CF₂H 1  A1288 2,2-dichlorocycloprop-1-yl H H CF₂H 1  A1289 (CH₃)₂NCH₂ H H CF₂H 1  A1290 HOCH₂ H H CF₂H 1  A1291 CH₃C(O)OCH₂ H H CF₂H 1  A1292 PhC(O)OCH₂ H H CF₂H 1  A1293 PhCH₂ H H CF₂H 1  A1294 CH₃OC(O)CH₂ H H CF₂H 1  A1295 NCCH₂ H H CF₂H 1  A1296 CH₃(CH₂)₇SO₂CH₂ H H CF₂H 1  A1297 Br H H CF₂H 1  A1298 Cl H H CF₂H 1  A1299 O═CHCH₂ H H CF₂H 1  A1300 CH₃ H H CF₃CF₂ 1  A1301 HO H Ph CF₃ 0  A1302 CH₃ H CH₂═CH CF₃ 0  A1303 CH₃ H CH₃CH₂O CF₃ 0  A1304 HO CH₃ H CF₃ 0  A1305 HO H H CF₃ 0  A1306 (CH₃CH₂)₂N(O)CO H H CF₃ 0  A1307 CH₃ H Tosyl-O CF₃ 0  A1308 CH₃ H CH₃CC CF₃ 0  A1309 CH₃ H HCC CF₃ 0  A1310 CH₃ H ClCH₂CC CF₃ 0  A1311 CH₃ H PhCH₂O CF₃ 0  A1312 CH₃ H CF₃SO₂O CF₃ 0  A1313 CH₃ H (CH₃)₂N CF₃ 0  A1314 CH₃ H CH₃C(O)O CF₃ 0  A1315 CH₃ H CH₃CH₂C(O)O CF₃ 0  A1316 CH₃ H PhC(O)O CF₃ 0  A1317 CH₃ H 3-Pyridyl CF₃ 0  A1318 CH₃OCH₂OCH₂ H H CF₂Cl 0  A1319 CH₃OCH₂OCH₂ H H CF₂H 0  A1320 CH₃OCH₂OCH₂ H H CF₂CF₃ 0  A1321 CH₃OCH₂OCH₂ H H CF₃ 1  A1322 CH₃O H CH₃ CF₃ 0

In Table 2 which follows, Q is C₁

and Q₁ the radicals B which follow:

TABLE 2 Radicals B: Radical R₆ R₇ R₈ R₉ R₁₀ W B1 H H H H OH CH₂ B2 CH₃ H H H OH CH₂ B3 CH₃CH₂ H H H OH CH₂ B4 CH₃CH₂CH₂ H H H OH CH₂ B5 (CH₃)₂CH H H H OH CH₂ B6 (CH₃)₃C H H H OH CH₂ B7 CH₃S H H H OH CH₂ B8 CH₃SO H H H OH CH₂ B9 CH₃SO₂ H H H OH CH₂ B10 Ph H H H OH CH₂ B11 CH₃O H H H OH CH₂ B12 CH₃OC(O) H H H OH CH₂ B13 CH₃CH₂OC(O) H H H OH CH₂ B14 CH₂═CHCH₂ H H H OH CH₂ B15 HCCCH₂ H H H OH CH₂ B16 CF₃ H H H OH CH₂ B17 (CH₃)₂NSO₂ H H H OH CH₂ B18 (CH₃)₂N H H H OH CH₂ B19 PhO H H H OH CH₂ B20 PhS H H H OH CH₂ B21 PhSO H H H OH CH₂ B22 PhSO₂ H H H OH CH₂ B23 CN H H H OH CH₂ B24 CH₃ CH₃ H H OH CH₂ B25 CH₃CH₂ CH₃ H H OH CH₂ B26 CH₃CH₂CH₂ CH₃ H H OH CH₂ B27 (CH₃)₂CH CH₃ H H OH CH₂ B28 (CH₃)₃C CH₃ H H OH CH₂ B29 CH₃S CH₃ H H OH CH₂ B30 CH₃SO CH₃ H H OH CH₂ B31 CH₃SO₂ CH₃ H H OH CH₂ B32 Ph CH₃ H H OH CH₂ B33 CH₃O CH₃ H H OH CH₂ B34 CH₃OC(O) CH₃ H H OH CH₂ B35 CH₃CH₂OC(O) CH₃ H H OH CH₂ B36 CH₂═CHCH₂ CH₃ H H OH CH₂ B37 HCCCH₂ CH₃ H H OH CH₂ B38 CF₃ CH₃ H H OH CH₂ B39 (CH₃)₂NSO₂ CH₃ H H OH CH₂ B40 (CH₃)₂N CH₃ H H OH CH₂ B41 PhO CH₃ H H OH CH₂ B42 PhS CH₃ H H OH CH₂ B43 PhSO CH₃ H H OH CH₂ B44 PhSO₂ CH₃ H H OH CH₂ B45 CN CH₃ H H OH CH₂ B46 CH₃ H CH₃ H OH CH₂ B47 CH₃CH₂ H CH₃ H OH CH₂ B48 CH₃CH₂CH₂ H CH₃ H OH CH₂ B49 (CH₃)₂CH H CH₃ H OH CH₂ B50 (CH₃)₃C H CH₃ H OH CH₂ B51 CH₃S H CH₃ H OH CH₂ B52 CH₃SO H CH₃ H OH CH₂ B53 CH₃SO₂ H CH₃ H OH CH₂ B54 Ph H CH₃ H OH CH₂ B55 CH₃O H CH₃ H OH CH₂ B56 CH₃OC(O) H CH₃ H OH CH₂ B57 CH₃CH₂OC(O) H CH₃ H OH CH₂ B58 CH₂═CHCH₂ H CH₃ H OH CH₂ B59 HCCCH₂ H CH₃ H OH CH₂ B60 CF₃ H CH₃ H OH CH₂ B61 (CH₃)₂NSO₂ H CH₃ H OH CH₂ B62 (CH₃)₂N H CH₃ H OH CH₂ B63 PhO H CH₃ H OH CH₂ B64 PhS H CH₃ H OH CH₂ B65 PhSO H CH₃ H OH CH₂ B66 PhSO₂ H CH₃ H OH CH₂ B67 CN H CH₃ H OH CH₂ B68 CH₃ CH₃ CH₃ H OH CH₂ B69 CH₃CH₂ CH₃ CH₃ H OH CH₂ B70 CH₃CH₂CH₂ CH₃ CH₃ H OH CH₂ B71 (CH₃)₂CH CH₃ CH₃ H OH CH₂ B72 (CH₃)₃C CH₃ CH₃ H OH CH₂ B73 CH₃S CH₃ CH₃ H OH CH₂ B74 CH₃SO CH₃ CH₃ H OH CH₂ B75 CH₃SO₂ CH₃ CH₃ H OH CH₂ B76 Ph CH₃ CH₃ H OH CH₂ B77 CH₃O CH₃ CH₃ H OH CH₂ B78 CH₃OC(O) CH₃ CH₃ H OH CH₂ B79 CH₃CH₂OC(O) CH₃ CH₃ H OH CH₂ B80 CH₂═CHCH₂ CH₃ CH₃ H OH CH₂ B81 HCCCH₂ CH₃ CH₃ H OH CH₂ B82 CF₃ CH₃ CH₃ H OH CH₂ B83 (CH₃)₂NSO₂ CH₃ CH₃ H OH CH₂ B84 (CH₃)₂N CH₃ CH₃ H OH CH₂ B85 PhO CH₃ CH₃ H OH CH₂ B86 PhS CH₃ CH₃ H OH CH₂ B87 PhSO CH₃ CH₃ H OH CH₂ B88 PhSO₂ CH₃ CH₃ H OH CH₂ B89 CN CH₃ CH₃ H OH CH₂ B90 CH₃ CH₃ CH₃ CH₃ OH CH₂ B91 CH₃CH₂ CH₃ CH₃ CH₃ OH CH₂ B92 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH CH₂ B93 (CH₃)₂CH CH₃ CH₃ CH₃ OH CH₂ B94 (CH₃)₃C CH₃ CH₃ CH₃ OH CH₂ B95 CH₃S CH₃ CH₃ CH₃ OH CH₂ B96 CH₃SO CH₃ CH₃ CH₃ OH CH₂ B97 CH₃SO₂ CH₃ CH₃ CH₃ OH CH₂ B98 Ph CH₃ CH₃ CH₃ OH CH₂ B99 CH₃O CH₃ CH₃ CH₃ OH CH₂ B100 CH₃OC(O) CH₃ CH₃ CH₃ OH CH₂ B101 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH CH₂ B102 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH CH₂ B103 HCCCH₂ CH₃ CH₃ CH₃ OH CH₂ B104 CF₃ CH₃ CH₃ CH₃ OH CH₂ B105 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH CH₂ B106 (CH₃)₂N CH₃ CH₃ CH₃ OH CH₂ B107 PhO CH₃ CH₃ CH₃ OH CH₂ B108 PhS CH₃ CH₃ CH₃ OH CH₂ B109 PhSO CH₃ CH₃ CH₃ OH CH₂ B110 PhSO₂ CH₃ CH₃ CH₃ OH CH₂ B111 CN CH₃ CH₃ CH₃ OH CH₂ B112 CH₃CH₂ CH₃CH₂ H H OH CH₂ B113 CH₃CH₂CH₂ CH₃CH₂ H H OH CH₂ B114 (CH₃)₂CH CH₃CH₂ H H OH CH₂ B115 (CH₃)₃C CH₃CH₂ H H OH CH₂ B116 CH₃S CH₃CH₂ H H OH CH₂ B117 CH₃SO CH₃CH₂ H H OH CH₂ B118 CH₃SO₂ CH₃CH₂ H H OH CH₂ B119 Ph CH₃CH₂ H H OH CH₂ B120 CH₃O CH₃CH₂ H H OH CH₂ B121 CH₃OC(O) CH₃CH₂ H H OH CH₂ B122 CH₃CH₂OC(O) CH₃CH₂ H H OH CH₂ B123 CH₂═CHCH₂ CH₃CH₂ H H OH CH₂ B124 HCCCH₂ CH₃CH₂ H H OH CH₂ B125 CF₃ CH₃CH₂ H H OH CH₂ B126 (CH₃)₂NSO₂ CH₃CH₂ H H OH CH₂ B127 (CH₃)₂N CH₃CH₂ H H OH CH₂ B128 PhO CH₃CH₂ H H OH CH₂ B129 PhS CH₃CH₂ H H OH CH₂ B130 PhSO CH₃CH₂ H H OH CH₂ B131 PhSO₂ CH₃CH₂ H H OH CH₂ B132 CN CH₃CH₂ H H OH CH₂ B133 H H H H OH CHCH₃ B134 CH₃ H H H OH CHCH₃ B135 CH₃CH₂ H H H OH CHCH₃ B136 CH₃CH₂CH₂ H H H OH CHCH₃ B137 (CH₃)₂CH H H H OH CHCH₃ B138 (CH₃)₃C H H H OH CHCH₃ B139 CH₃S H H H OH CHCH₃ B140 CH₃SO H H H OH CHCH₃ B141 CH₃SO₂ H H H OH CHCH₃ B142 Ph H H H OH CHCH₃ B143 CH₃O H H H OH CHCH₃ B144 CH₃OC(O) H H H OH CHCH₃ B145 CH₃CH₂OC(O) H H H OH CHCH₃ B146 CH₂═CHCH₂ H H H OH CHCH₃ B147 HCCCH₂ H H H OH CHCH₃ B148 CF₃ H H H OH CHCH₃ B149 (CH₃)₂NSO₂ H H H OH CHCH₃ B150 (CH₃)₂N H H H OH CHCH₃ B151 PhO H H H OH CHCH₃ B152 PhS H H H OH CHCH₃ B153 PhSO H H H OH CHCH₃ B154 PhSO₂ H H H OH CHCH₃ B155 CN H H H OH CHCH₃ B156 CH₃ CH₃ H H OH CHCH₃ B157 CH₃CH₂ CH₃ H H OH CHCH₃ B158 CH₃CH₂CH₂ CH₃ H H OH CHCH₃ B159 (CH₃)₂CH CH₃ H H OH CHCH₃ B160 (CH₃)₃C CH₃ H H OH CHCH₃ B161 CH₃S CH₃ H H OH CHCH₃ B162 CH₃SO CH₃ H H OH CHCH₃ B163 CH₃SO₂ CH₃ H H OH CHCH₃ B164 Ph CH₃ H H OH CHCH₃ B165 CH₃O CH₃ H H OH CHCH₃ B166 CH₃OC(O) CH₃ H H OH CHCH₃ B167 CH₃CH₂OC(O) CH₃ H H OH CHCH₃ B168 CH₂═CHCH₂ CH₃ H H OH CHCH₃ B169 HCCCH₂ CH₃ H H OH CHCH₃ B170 CF₃ CH₃ H H OH CHCH₃ B171 (CH₃)₂NSO₂ CH₃ H H OH CHCH₃ B172 (CH₃)₂N CH₃ H H OH CHCH₃ B173 PhO CH₃ H H OH CHCH₃ B174 PhS CH₃ H H OH CHCH₃ B175 PhSO CH₃ H H OH CHCH₃ B176 PhSO₂ CH₃ H H OH CHCH₃ B177 CN CH₃ H H OH CHCH₃ B178 CH₃ H CH₃ H OH CHCH₃ B179 CH₃CH₂ H CH₃ H OH CHCH₃ B180 CH₃CH₂CH₂ H CH₃ H OH OHCH₃ B181 (CH₃)₂CH H CH₃ H OH CHCH₃ B182 (CH₃)₃C H CH₃ H OH CHCH₃ B183 CH₃S H CH₃ H OH CHCH₃ B184 CH₃SO H CH₃ H OH CHCH₃ B185 CH₃SO₂ H CH₃ H OH CHCH₃ B186 Ph H CH₃ H OH CHCH₃ B187 CH₃O H CH₃ H OH CHCH₃ B188 CH₃OC(O) H CH₃ H OH CHCH₃ B189 CH₃CH₂OC(O) H CH₃ H OH CHCH₃ B190 CH₂═CHCH₂ H CH₃ H OH CHCH₃ B191 HCCCH₂ H CH₃ H OH CHCH₃ B192 CF₃ H CH₃ H OH CHCH₃ B193 (CH₃)₂NSO₂ H CH₃ H OH CHCH₃ B194 (CH₃)₂N H CH₃ H OH CHCH₃ B195 PhO H CH₃ H OH CHCH₃ B196 PhS H CH₃ H OH CHCH₃ B197 PhSO H CH₃ H OH CHCH₃ B198 PhSO₂ H CH₃ H OH CHCH₃ B199 CN H CH₃ H OH CHCH₃ B200 CH₃ CH₃ CH₃ H OH CHCH₃ B201 CH₃CH₂ CH₃ CH₃ H OH CHCH₃ B202 CH₃CH₂CH₂ CH₃ CH₃ H OH CHCH₃ B203 (CH₃)₂CH CH₃ CH₃ H OH CHCH₃ B204 (CH₃)₃C CH₃ CH₃ H OH CHCH₃ B205 CH₃S CH₃ CH₃ H OH CHCH₃ B206 CH₃SO CH₃ CH₃ H OH CHCH₃ B207 CH₃SO₂ CH₃ CH₃ H OH CHCH₃ B208 Ph CH₃ CH₃ H OH CHCH₃ B209 CH₃O CH₃ CH₃ H OH CHCH₃ B210 CH₃OC(O) CH₃ CH₃ H OH CHCH₃ B211 CH₃CH₂OC(O) CH₃ CH₃ H OH CHCH₃ B212 CH₂═CHCH₂ CH₃ CH₃ H OH CHCH₃ B213 HCCCH₂ CH₃ CH₃ H OH CHCH₃ B214 CF₃ CH₃ CH₃ H OH CHCH₃ B215 (CH₃)₂NSO₂ CH₃ CH₃ H OH CHCH₃ B216 (CH₃)₂N CH₃ CH₃ H OH CHCH₃ B217 PhO CH₃ CH₃ H OH CHCH₃ B218 PhS CH₃ CH₃ H OH CHCH₃ B219 PhSO CH₃ CH₃ H OH CHCH₃ B220 PhSO₂ CH₃ CH₃ H OH CHCH₃ B221 CN CH₃ CH₃ H OH CHCH₃ B222 CH₃ CH₃ CH₃ CH₃ OH CHCH₃ B223 CH₃CH₂ CH₃ CH₃ CH₃ OH CHCH₃ B224 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH CHCH₃ B225 (CH₃)₂CH CH₃ CH₃ CH₃ OH CHCH₃ B226 (CH₃)₃C CH₃ CH₃ CH₃ OH CHCH₃ B227 CH₃S CH₃ CH₃ CH₃ OH CHCH₃ B228 CH₃SO CH₃ CH₃ CH₃ OH CHCH₃ B229 CH₃SO₂ CH₃ CH₃ CH₃ OH CHCH₃ B230 Ph CH₃ CH₃ CH₃ OH CHCH₃ B231 CH₃O CH₃ CH₃ CH₃ OH CHCH₃ B232 CH₃OC(O) CH₃ CH₃ CH₃ OH CHCH₃ B233 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH CHCH₃ B234 CH₂=CHCH₂ CH₃ CH₃ CH₃ OH CHCH₃ B235 HCCCH₂ CH₃ CH₃ CH₃ OH CHCH₃ B236 CF₃ CH₃ CH₃ CH₃ OH CHCH₃ B237 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH CHCH₃ B238 (CH₃)₂N CH₃ CH₃ CH₃ OH CHCH₃ B239 PhO CH₃ CH₃ CH₃ OH CHCH₃ B240 PhS CH₃ CH₃ OH₃ OH CHCH₃ B241 PhSO CH₃ CH₃ CH₃ OH CHCH₃ B242 PhSO₂ CH₃ CH₃ CH₃ OH CHCH₃ B243 CN CH₃ CH₃ CH₃ OH CHCH₃ B244 CH₃CH₂ CH₃CH₂ H H OH CHCH₃ B245 CH₃CH₂CH₂ CH₃CH₂ H H OH CHCH₃ B246 (CH₃)₂CH CH₃CH₂ H H OH CHCH₃ B247 (CH₃)₃C CH₃CH₂ H H OH CHCH₃ B248 CH₃S CH₃CH₂ H H OH CHCH₃ B249 CH₃SO CH₃CH₂ H H OH CHCH₃ B250 CH₃SO₂ CH₃CH₂ H H OH CHCH₃ B251 Ph CH₃CH₂ H H OH CHCH₃ B252 CH₃O CH₃CH₂ H H OH CHCH₃ B253 CH₃OC(O) CH₃CH₂ H H OH CHCH₃ B254 CH₃CH₂OC(O) CH₃CH₂ H H OH CHCH₃ B255 CH₂═CHCH₂ CH₃CH₂ H H OH CHCH₃ B256 HCCCH₂ CH₃CH₂ H H OH CHCH₃ B257 CF₃ CH₃CH₂ H H OH CHCH₃ B258 (CH₃)₂NSO₂ CH₃CH₂ H H OH CHCH₃ B259 (CH₃)₂N CH₃CH₂ H H OH CHCH₃ B260 PhO CH₃CH₂ H H OH CHCH₃ B261 PhS CH₃CH₂ H H OH CHCH₃ B262 PhSO CH₃CH₂ H H OH CHCH₃ B263 PhSO₂ CH₃CH₂ H H OH CHCH₃ B264 CN CH₃CH₂ H H OH CHCH₃ B265 H H H H OH C═O B266 CH₃ H H H OH C═O B267 CH₃CH₂ H H H OH C═O B268 CH₃CH₂CH₂ H H H OH C═O B269 (CH₃)₂CH H H H OH C═O B270 (CH₃)₃C H H H OH C═O B271 CH₃S H H H OH C═O B272 CH₃SO H H H OH C═O B273 CH₃SO₂ H H H OH C═O B274 Ph H H H OH C═O B275 CH₃O H H H OH C═O B276 CH₃OC(O) H H H OH C═O B277 CH₃CH₂OC(O) H H H OH C═O B278 CH₂═CHCH₂ H H H OH C═O B279 HCCCH₂ H H H OH C═O B280 CF₃ H H H OH C═O B281 (CH₃)₂NSO₂ H H H OH C═O B282 (CH₃)₂N H H H OH C═O B283 PhO H H H OH C═O B284 PhS H H H OH C═O B285 PhSO H H H OH C═O B286 PhSO₂ H H H OH C═O B287 CN H H H OH C═O B288 CH₃ CH₃ H H OH C═O B289 CH₃CH₂ CH₃ H H OH C═O B290 CH₃CH₂CH₂ CH₃ H H OH C═O B291 (CH₃)₂CH CH₃ H H OH C═O B292 (CH₃)₃C CH₃ H H OH C═O B293 CH₃S CH₃ H H OH C═O B294 CH₃SO CH₃ H H OH C═O B295 CH₃SO₂ CH₃ H H OH C═O B296 Ph CH₃ H H OH C═O B297 CH₃O CH₃ H H OH C═O B298 CH₃OC(O) CH₃ H H OH C═O B299 CH₃CH₂OC(O) CH₃ H H OH C═O B300 CH₂═CHCH₂ CH₃ H H OH C═O B301 HCCCH₂ CH₃ H H OH C═O B302 CF₃ CH₃ H H OH C═O B303 (CH₃)₂NSO₂ CH₃ H H OH C═O B304 (CH₃)₂N CH₃ H H OH C═O B305 PhO CH₃ H H OH C═O B306 PhS CH₃ H H OH C═O B307 PhSO CH₃ H H OH C═O B308 PhSO₂ CH₃ H H OH C═O B309 CN CH₃ H H OH C═O B310 CH₃ H CH₃ H OH C═O B311 CH₃CH₂ H CH₃ H OH C═O B312 CH₃CH₂CH₂ H CH₃ H OH C═O B313 (CH₃)₂CH H CH₃ H OH C═O B314 (CH₃)₃C H CH₃ H OH C═O B315 CH₃S H CH₃ H OH C═O B316 CH₃SO H CH₃ H OH C═O B317 CH₃SO₂ H CH₃ H OH C═O B318 Ph H CH₃ H OH C═O B319 CH₃O H CH₃ H OH C═O B320 CH₃OC(O) H CH₃ H OH C═O B321 CH₃CH₂OC(O) H CH₃ H OH C═O B322 CH₂═CHCH₂ H CH₃ H OH C═O B323 HCCCH₂ H CH₃ H OH C═O B324 CF₃ H CH₃ H OH C═O B325 (CH₃)₂NSO₂ H CH₃ H OH C═O B326 (CH₃)₂N H CH₃ H OH C═O B327 PhO H CH₃ H OH C═O B328 PhS H CH₃ H OH C═O B329 PhSO H CH₃ H OH C═O B330 PhSO₂ H CH₃ H OH C═O B331 CN H CH₃ H OH C═O B332 CH₃ CH₃ CH₃ H OH C═O B333 CH₃CH₂ CH₃ CH₃ H OH C═O B334 CH₃CH₂CH₂ CH₃ CH₃ H OH C═O B335 (CH₃)₂CH CH₃ CH₃ H OH C═O B336 (CH₃)₃C CH₃ CH₃ H OH C═O B337 CH₃S CH₃ CH₃ H OH C═O B338 CH₃SO CH₃ CH₃ H OH C═O B339 CH₃SO₂ CH₃ CH₃ H OH C═O B340 Ph CH₃ CH₃ H OH C═O B341 CH₃O CH₃ CH₃ H OH C═O B342 CH₃OC(O) CH₃ CH₃ H OH C═O B343 CH₃CH₂OC(O) CH₃ CH₃ H OH C═O B344 CH₂═CHCH₂ CH₃ CH₃ H OH C═O B345 HCCCH₂ CH₃ CH₃ H OH C═O B346 CF₃ CH₃ CH₃ H OH C═O B347 (CH₃)₂NSO₂ CH₃ CH₃ H OH C═O B348 (CH₃)₂N CH₃ CH₃ H OH C═O B349 PhO CH₃ CH₃ H OH C═O B350 PhS CH₃ CH₃ H OH C═O B351 PhSO CH₃ CH₃ H OH C═O B352 PhSO₂ CH₃ CH₃ H OH C═O B353 CN CH₃ CH₃ H OH C═O B354 CH₃ CH₃ CH₃ CH₃ OH C═O B355 CH₃CH₂ CH₃ CH₃ CH₃ OH C═O B356 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH C═O B357 (CH₃)₂CH CH₃ CH₃ CH₃ OH C═O B358 (CH₃)₃C CH₃ CH₃ CH₃ OH C═O B359 CH₃S CH₃ CH₃ CH₃ OH C═O B360 CH₃SO CH₃ CH₃ CH₃ OH C═O B361 CH₃SO₂ CH₃ CH₃ CH₃ OH C═O B362 Ph CH₃ CH₃ CH₃ OH C═O B363 CH₃O CH₃ CH₃ CH₃ OH C═O B364 CH₃OC(O) CH₃ CH₃ CH₃ OH C═O B365 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH C═O B366 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH C═O B367 HCCCH₂ CH₃ CH₃ CH₃ OH C═O B368 CF₃ CH₃ CH₃ CH₃ OH C═O B369 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH C═O B370 (CH₃)₂N CH₃ CH₃ CH₃ OH C═O B371 PhO CH₃ CH₃ CH₃ OH C═O B372 PhS CH₃ CH₃ CH₃ OH C═O B373 PhSO CH₃ CH₃ CH₃ OH C═O B374 PhSO₂ CH₃ CH₃ CH₃ OH C═O B375 CN CH₃ CH₃ CH₃ OH C═O B376 CH₃CH₂ CH₃CH₂ H H OH C═O B377 CH₃CH₂CH₂ CH₃CH₂ H H OH C═O B378 (CH₃)₂CH CH₃CH₂ H H OH C═O B379 (CH₃)₃C CH₃CH₂ H H OH C═O B380 CH₃S CH₃CH₂ H H OH C═O B381 CH₃SO CH₃CH₂ H H OH C═O B382 CH₃SO₂ CH₃CH₂ H H OH C═O B383 Ph CH₃CH₂ H H OH C═O B384 CH₃O CH₃CH₂ H H OH C═O B385 CH₃OC(O) CH₃CH₂ H H OH C═O B386 CH₃CH₂OC(O) CH₃CH₂ H H OH C═O B387 CH₂═CHCH₂ CH₃CH₂ H H OH C═O B388 HCCCH₂ CH₃CH₂ H H CH C═O B389 CF₃ CH₃CH₂ H H OH C═O B390 (CH₃)₂NSO₂ CH₃CH₂ H H OH C═O B391 (CH₃)₂N CH₃CH₂ H H OH C═O B392 PhO CH₃CH₂ H H OH C═O B393 PhS CH₃CH₂ H H OH C═O B394 PhSO CH₃CH₂ H H OH C═O B395 PhSO₂ CH₃CH₂ H H OH C═O B396 CN CH₃CH₂ H H OH C═O B397 H H H H OH N—CH₃ B398 CH₃ H H H OH N—CH₃ B399 CH₃CH₂ H H H OH N—CH₃ B400 CH₃CH₂CH₂ H H H OH N—CH₃ B401 (CH₃)₂CH H H H OH N—CH₃ B402 (CH₃)₃C H H H OH N—CH₃ B403 CH₃S H H H OH N—CH₃ B404 CH₃SO H H H OH N—CH₃ B405 CH₃SO₂ H H H OH N—CH₃ B406 Ph H H H OH N—CH₃ B407 CH₃O H H H OH N—CH₃ B408 CH₃OC(O) H H H OH N—CH₃ B409 CH₃CH₂OC(O) H H H OH N—CH₃ B410 CH₂═CHCH₂ H H H OH N—CH₃ B411 HCCCH₂ H H H OH N—CH₃ B412 CF₃ H H H OH N—CH₃ B413 (CH₃)₂NSO₂ H H H OH N—CH₃ B414 (CH₃)₂N H H H OH N—CH₃ B415 PhO H H H OH N—CH₃ B416 PhS H H H OH N—CH₃ B417 PhSO H H H OH N—CH₃ B418 PhSO₂ H H H OH N—CH₃ B419 CN H H H OH N—CH₃ B420 CH₃ CH₃ H H OH N—CH₃ B421 CH₃CH₂ CH₃ H H OH N—CH₃ B422 CH₃CH₂CH₂ CH₃ H H OH N—CH₃ B423 (CH₃)₂CH CH₃ H H OH N—CH₃ B424 (CH₃)₃C CH₃ H H OH N—CH₃ B425 CH₃S CH₃ H H OH N—CH₃ B426 CH₃SO CH₃ H H OH N—CH₃ B427 CH₃SO₂ CH₃ H H OH N—CH₃ B428 Ph CH₃ H H OH N—CH₃ B429 CH₃O CH₃ H H OH N—CH₃ B430 CH₃OC(O) CH₃ H H OH N—CH₃ B431 CH₃CH₂OC(O) CH₃ H H OH N—CH₃ B432 CH₂═CHCH₂ CH₃ H H OH N—CH₃ B433 HCCCH₂ CH₃ H H OH N—CH₃ B434 CF₃ CH₃ H H OH N—CH₃ B435 (CH₃)₂NSO₂ CH₃ H H OH N—CH₃ B436 (CH₃)₂N CH₃ H H OH N—CH₃ B437 PhO CH₃ H H OH N—CH₃ B438 PhS CH₃ H H OH N—CH₃ B439 PhSO CH₃ H H OH N—CH₃ B440 PhSO₂ CH₃ H H OH N—CH₃ B441 CN CH₃ H H OH N—CH₃ B442 CH₃ H CH₃ H OH N—CH₃ B443 CH₃CH₂ H CH₃ H OH N—CH₃ B444 CH₃CH₂CH₂ H CH₃ H OH N—CH₃ B445 (CH₃)₂CH H CH₃ H OH N—CH₃ B446 (CH₃)₃C H CH₃ H OH N—CH₃ B447 CH₃S H CH₃ H OH N—CH₃ B448 CH₃SO H CH₃ H OH N—CH₃ B449 CH₃SO₂ H CH₃ H OH N—CH₃ B450 Ph H CH₃ H OH N—CH₃ B451 CH₃O H CH₃ H OH N—CH₃ B452 CH₃OC(O) H CH₃ H OH N—CH₃ B453 CH₃CH₂OC(O) H CH₃ H OH N—CH₃ B454 CH₂═CHCH₂ H CH₃ H OH N—CH₃ B455 HCCCH₂ H CH₃ H OH N—CH₃ B456 CF₃ H CH₃ H OH N—CH₃ B457 (CH₃)₂NSO₂ H CH₃ H OH N—CH₃ B458 (CH₃)₂N H CH₃ H OH N—CH₃ B459 PhO H CH₃ H OH N—CH₃ B460 PhS H CH₃ H OH N—CH₃ B461 PhSO H CH₃ H OH N—CH₃ B462 PhSO₂ H CH₃ H OH N—CH₃ B463 CN H CH₃ H OH N—CH₃ B464 CH₃ CH₃ CH₃ H OH N—CH₃ B465 CH₃CH₂ CH₃ CH₃ H OH N—CH₃ B466 CH₃CH₂CH₂ CH₃ CH₃ H OH N—CH₃ B467 (CH₃)₂CH CH₃ CH₃ H OH N—CH₃ B468 (CH₃)₃C CH₃ CH₃ H OH N—CH₃ B469 CH₃S CH₃ CH₃ H OH N—CH₃ B470 CH₃SO CH₃ CH₃ H OH N—CH₃ B471 CH₃SO₂ CH₃ CH₃ H OH N—CH₃ B472 Ph CH₃ CH₃ H OH N—CH₃ B473 CH₃O CH₃ CH₃ H OH N—CH₃ B474 CH₃OC(O) CH₃ CH₃ H OH N—CH₃ B475 CH₃CH₂OC(O) CH₃ CH₃ H OH N—CH₃ B476 CH₂═CHCH₂ CH₃ CH₃ H OH N—CH₃ B477 HCCCH₂ CH₃ CH₃ H OH N—CH₃ B478 CF₃ CH₃ CH₃ H OH N—CH₃ B479 (CH₃)₂NSO₂ CH₃ CH₃ H OH N—CH₃ B480 (CH₃)₂N CH₃ CH₃ H OH N—CH₃ B481 PhO CH₃ CH₃ H OH N—CH₃ B482 PhS CH₃ CH₃ H OH N—CH₃ B483 PhSO CH₃ CH₃ H OH N—CH₃ B484 PhSO₂ CH₃ CH₃ H OH N—CH₃ B485 CN CH₃ CH₃ H OH N—CH₃ B486 CH₃ CH₃ CH₃ CH₃ OH N—CH₃ B487 CH₃CH₂ CH₃ CH₃ CH₃ OH N—CH₃ B488 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH N—CH₃ B489 (CH₃)₂CH CH₃ CH₃ CH₃ OH N—CH₃ B490 (CH₃)₃C CH₃ CH₃ CH₃ OH N—CH₃ B491 CH₃S CH₃ CH₃ CH₃ OH N—CH₃ B492 CH₃SO CH₃ CH₃ CH₃ OH N—CH₃ B493 CH₃SO₂ CH₃ CH₃ CH₃ OH N—CH₃ B494 Ph CH₃ CH₃ CH₃ OH N—CH₃ B495 CH₃O CH₃ CH₃ CH₃ OH N—CH₃ B496 CH₃OC(O) CH₃ CH₃ CH₃ OH N—CH₃ B497 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH N—CH₃ B498 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH N—CH₃ B499 HCCCH₂ CH₃ CH₃ CH₃ OH N—CH₃ B500 CF₃ CH₃ CH₃ CH₃ OH N—CH₃ B501 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH N—CH₃ B502 (CH₃)₂N CH₃ CH₃ CH₃ OH N—CH₃ B503 PhO CH₃ CH₃ CH₃ OH N—CH₃ B504 PhS CH₃ CH₃ CH₃ OH N—CH₃ B505 PhSO CH₃ CH₃ CH₃ OH N—CH₃ B506 PhSO₂ CH₃ CH₃ CH₃ OH N—CH₃ B507 CN CH₃ CH₃ CH₃ OH N—CH₃ B508 CH₃CH₂ CH₃CH₂ H H OH N—CH₃ B509 CH₃CH₂CH₂ CH₃CH₂ H H OH N—CH₃ B510 (CH₃)₂CH CH₃CH₂ H H OH N—CH₃ B511 (CH₃)₃C CH₃CH₂ H H OH N—CH₃ B512 CH₃S CH₃CH₂ H H OH N—CH₃ B513 CH₃SO CH₃CH₂ H H OH N—CH₃ B514 CH₃SO₂ CH₃CH₂ H H OH N—CH₃ B515 Ph CH₃CH₂ H H OH N—CH₃ B516 CH₃O CH₃CH₂ H H OH N—CH₃ B517 CH₃OC(O) CH₃CH₂ H H OH N—CH₃ B518 CH₃CH₂OC(O) CH₃CH₂ H H OH N—CH₃ B519 CH₂═CHCH₂ CH₃CH₂ H H OH N—CH₃ B520 HCCCH₂ CH₃CH₂ H H OH N—CH₃ B521 CF₃ CH₃CH₂ H H OH N—CH₃ B522 (CH₃)₂NSO₂ CH₃CH₂ H H OH N—CH₃ B523 (CH₃)₂N CH₃CH₂ H H OH N—CH₃ B524 PhO CH₃CH₂ H H OH N—CH₃ B525 PhS CH₃CH₂ H H OH N—CH₃ B526 PhSO CH₃CH₂ H H OH N—CH₃ B527 PhSO₂ CH₃CH₂ H H OH N—CH₃ B528 CN CH₃CH₂ H H OH N—CH₃ B529 H H H H OH O B530 CH₃ H H H OH O B531 CH₃CH₂ H H H OH O B532 CH₃CH₂CH₂ H H H OH O B533 (CH₃)₂CH H H H OH O B534 (CH₃)₃C H H H OH O B535 CH₃S H H H OH O B536 CH₃SO H H H OH O B537 CH₃SO₂ H H H OH O B538 Ph H H H OH O B539 CH₃O H H H OH O B540 CH₃OC(O) H H H OH O B541 CH₃CH₂OC(O) H H H OH O B542 CH₂═CHCH₂ H H H OH O B543 HCCCH₂ H H H OH O B544 CF₃ H H H OH O B545 (CH₃)₂NSO₂ H H H OH O B546 (CH₃)₂N H H H OH O B547 PhO H H H OH O B548 PhS H H H OH O B549 PhSO H H H OH O B550 PhSO₂ H H H OH O B551 CN H H H OH O B552 CH₃ CH₃ H H OH O B553 CH₃CH₂ CH₃ H H OH O B554 CH₃CH₂CH₂ CH₃ H H OH O B555 (CH₃)₂CH CH₃ H H OH O B556 (CH₃)₃C CH₃ H H OH O B557 CH₃S CH₃ H H OH O B558 CH₃SO CH₃ H H OH O B559 CH₃SO₂ CH₃ H H OH O B560 Ph CH₃ H H OH O B561 CH₃O CH₃ H H OH O B562 CH₃OC(O) CH₃ H H OH O B563 CH₃CH₂OC(O) CH₃ H H OH O B564 CH₂═CHCH₂ CH₃ H H OH O B565 HCCCH₂ CH₃ H H OH O B566 CF₃ CH₃ H H OH O B567 (CH₃)₂NSO₂ CH₃ H H OH O B568 (CH₃)₂N CH₃ H H OH O B569 PhO CH₃ H H OH O B570 PhS CH₃ H H OH O B571 PhSO CH₃ H H OH O B572 PhSO₂ CH₃ H H OH O B573 CN CH₃ H H OH O B574 CH₃ H CH₃ H OH O B575 CH₃CH₂ H CH₃ H OH O B576 CH₃CH₂CH₂ H CH₃ H OH O B577 (CH₃)₂CH H CH₃ H OH O B578 (CH₃)₃C H CH₃ H OH O B579 CH₃S H CH₃ H OH O B580 CH₃SO H CH₃ H OH O B581 CH₃SO₂ H CH₃ H OH O B582 Ph H CH₃ H OH O B583 CH₃O H CH₃ H OH O B584 CH₃OC(O) H CH₃ H OH O B585 CH₃CH₂OC(O) H CH₃ H OH O B586 CH₂═CHCH₂ H CH₃ H OH O B587 HCCCH₂ H CH₃ H OH O B588 CF₃ H CH₃ H OH O B589 (CH₃)₂NSO₂ H CH₃ H OH O B590 (CH₃)₂N H CH₃ H OH O B591 PhO H CH₃ H OH O B592 PhS H CH₃ H OH O B593 PhSO H CH₃ H OH O B594 PhSO₂ H CH₃ H OH O B595 CN H CH₃ H OH O B596 CH₃ CH₃ CH₃ H OH O B597 CH₃CH₂ CH₃ CH₃ H OH O B598 CH₃CH₂CH₂ CH₃ CH₃ H OH O B599 (CH₃)₂CH CH₃ CH₃ H OH O B600 (CH₃)₃C CH₃ CH₃ H OH O B601 CH₃S CH₃ CH₃ H OH O B602 CH₃SO CH₃ CH₃ H OH O B603 CH₃SO₂ CH₃ OH₃ H OH O B604 Ph CH₃ CH₃ H OH O B605 CH₃O CH₃ CH₃ H OH O B606 CH₃OC(O) CH₃ CH₃ H OH O B607 CH₃CH₂OC(O) CH₃ CH₃ H OH O B608 CH₂═CHCH₂ CH₃ CH₃ H OH O B609 HCCCH₂ CH₃ CH₃ H OH O B610 CF₃ CH₃ CH₃ H OH O B611 (CH₃)₂NSO₂ CH₃ CH₃ H OH O B612 (CH₃)₂N CH₃ CH₃ H OH O B613 PhO CH₃ CH₃ H OH O B614 PhS CH₃ CH₃ H OH O B615 PhSO CH₃ CH₃ H OH O B616 PhSO₂ CH₃ CH₃ H OH O B617 CN CH₃ CH₃ H OH O B618 CH₃ CH₃ CH₃ CH₃ OH O B619 CH₃CH₂ CH₃ CH₃ CH₃ OH O B620 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH O B621 (CH₃)₂CH CH₃ CH₃ CH₃ OH O B622 (CH₃)₃C CH₃ CH₃ CH₃ OH O B623 CH₃S CH₃ CH₃ CH₃ OH O B624 CH₃SO CH₃ CH₃ CH₃ OH O B625 CH₃SO₂ CH₃ CH₃ CH₃ OH O B626 Ph CH₃ CH₃ CH₃ OH O B627 CH₃O CH₃ CH₃ CH₃ OH O B628 CH₃OC(O) CH₃ CH₃ CH₃ OH O B629 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH O B630 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH O B631 HCCCH₂ CH₃ CH₃ CH₃ OH O B632 CF₃ CH₃ CH₃ CH₃ OH O B633 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH O B634 (CH₃)₂N CH₃ CH₃ CH₃ OH O B635 PhO CH₃ CH₃ CH₃ OH O B636 PhS CH₃ CH₃ OH₃ OH O B637 PhSO CH₃ CH₃ CH₃ OH O B638 PhSO₂ CH₃ CH₃ CH₃ OH O B639 CN CH₃ CH₃ CH₃ OH O B640 CH₃CH₂ CH₃CH₂ H H OH O B641 CH₃CH₂CH₂ CH₃CH₂ H H OH O B642 (CH₃)₂CH CH₃CH₂ H H OH O B643 (CH₃)₃C CH₃CH₂ H H OH O B644 CH₃S CH₃CH₂ H H OH O B645 CH₃SO CH₃CH₂ H H OH O B646 CH₃SO₂ CH₃CH₂ H H OH O B647 Ph CH₃CH₂ H H OH O B648 CH₃O CH₃CH₂ H H OH O B649 CH₃OC(O) CH₃CH₂ H H OH O B650 CH₃CH₂OC(O) CH₃CH₂ H H OH O B651 CH₂═CHCH₂ CH₃CH₂ H H OH O B652 HCCCH₂ CH₃CH₂ H H OH O B653 CF₃ CH₃CH₂ H H OH O B654 (CH₃)₂NSO₂ CH₃CH₂ H H OH O B655 (CH₃)₂N CH₃CH₂ H H OH O B656 PhO CH₃CH₂ H H OH O B657 PhS CH₃CH₂ H H OH O B658 PhSO CH₃CH₂ H H OH O B659 PhSO₂ CH₃CH₂ H H OH O B660 CN CH₃CH₂ H H OH O B661 H H H H OH S B662 CH₃ H H H OH S B663 CH₃CH₂ H H H OH S B664 CH₃CH₂CH₂ H H H OH S B665 (CH₃)₂CH H H H OH S B666 (CH₃)₃C H H H OH S B667 CH₃S H H H OH S B668 CH₃SO H H H OH S B669 CH₃SO₂ H H H OH S B670 Ph H H H OH S B671 CH₃O H H H OH S B672 CH₃OC(O) H H H OH S B673 CH₃CH₂OC(O) H H H OH S B674 CH₂═CHCH₂ H H H OH S B675 HCCCH₂ H H H OH S B676 CF₃ H H H OH S B677 (CH₃)₂NSO₂ H H H OH S B678 (CH₃)₂N H H H OH S B679 PhO H H H OH S B680 PhS H H H OH S B681 PhSO H H H OH S B682 PhSO₂ H H H OH S B683 CN H H H OH S B684 CH₃ CH₃ H H OH S B685 CH₃CH₂ CH₃ H H OH S B686 CH₃CH₂CH₂ CH₃ H H OH S B687 (CH₃)₂CH CH₃ H H OH S B688 (CH₃)₃C CH₃ H H OH S B689 CH₃S CH₃ H H OH S B690 CH₃SO CH₃ H H OH S B691 CH₃SO₂ CH₃ H H OH S B692 Ph CH₃ H H OH S B693 CH₃O CH₃ H H OH S B694 CH₃OC(O) CH₃ H H OH S B695 CH₃CH₂OC(O) CH₃ H H OH S B696 CH₂═CHCH₂ CH₃ H H OH S B697 HCCCH₂ CH₃ H H OH S B698 CF₃ CH₃ H H OH S B699 (CH₃)₂NSO₂ CH₃ H H OH S B700 (CH₃)₂N CH₃ H H OH S B701 PhO CH₃ H H OH S B702 PhS CH₃ H H OH S B703 PhSO CH₃ H H OH S B704 PhSO₂ CH₃ H H OH S B705 CN CH₃ H H OH S B706 CH₃ H CH₃ H OH S B707 CH₃CH₂ H CH₃ H OH S B708 CH₃CH₂CH₂ H CH₃ H OH S B709 (CH₃)₂CH H CH₃ H OH S B710 (CH₃)₃C H CH₃ H OH S B711 CH₃S H CH₃ H OH S B712 CH₃SO H CH₃ H OH S B713 CH₃SO₂ H CH₃ H OH S B714 Ph H CH₃ H OH S B715 CH₃O H CH₃ H OH S B716 CH₃OC(O) H CH₃ H OH S B717 CH₃CH₂OC(O) H CH₃ H OH S B718 CH₂═CHCH₂ H CH₃ H OH S B719 HCCCH₂ H CH₃ H OH S B720 CF₃ H CH₃ H OH S B721 (CH₃)₂NSO₂ H CH₃ H OH S B722 (CH₃)₂N H CH₃ H OH S B723 PhO H CH₃ H OH S B724 PhS H CH₃ H OH S B725 PhSO H CH₃ H OH S B726 PhSO₂ H CH₃ H OH S B727 CN H CH₃ H OH S B728 CH₃ CH₃ CH₃ H OH S B729 CH₃CH₂ CH₃ CH₃ H OH S B730 CH₃CH₂CH₂ CH₃ CH₃ H OH S B731 (CH₃)₂CH CH₃ CH₃ H OH S B732 (CH₃)₃C CH₃ CH₃ H OH S B733 CH₃S CH₃ CH₃ H OH S B734 CH₃SO CH₃ CH₃ H OH S B735 CH₃SO₂ CH₃ CH₃ H OH S B736 Ph CH₃ CH₃ H OH S B737 CH₃O CH₃ CH₃ H OH S B738 CH₃OC(O) CH₃ CH₃ H OH S B739 CH₃CH₂OC(O) CH₃ CH₃ H OH S B740 CH₂═CHCH₂ CH₃ CH₃ H OH S B741 HCCCH₂ CH₃ CH₃ H OH S B742 CF₃ CH₃ CH₃ H OH S B743 (CH₃)₂NSO₂ CH₃ CH₃ H OH S B744 (CH₃)₂N CH₃ CH₃ H OH S B745 PhO CH₃ CH₃ H OH S B746 PhS CH₃ CH₃ H OH S B747 PhSO CH₃ CH₃ H OH S B748 PhSO₂ CH₃ CH₃ H OH S B749 CN CH₃ CH₃ H OH S B750 CH₃ CH₃ CH₃ CH₃ OH S B751 CH₃CH₂ CH₃ CH₃ CH₃ OH S B752 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH S B753 (CH₃)₂CH CH₃ CH₃ CH₃ OH S B754 (CH₃)₃C CH₃ CH₃ CH₃ OH S B755 CH₃S CH₃ CH₃ CH₃ OH S B756 CH₃SO CH₃ CH₃ CH₃ OH S B757 CH₃SO₂ CH₃ CH₃ CH₃ OH S B758 Ph CH₃ CH₃ CH₃ OH S B759 CH₃O CH₃ CH₃ CH₃ OH S B760 CH₃OC(O) CH₃ CH₃ CH₃ OH S B761 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH S B762 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH S B763 HCCCH₂ CH₃ CH₃ CH₃ OH S B764 CF₃ CH₃ CH₃ CH₃ OH S B765 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH S B766 (CH₃)₂N CH₃ CH₃ CH₃ OH S B767 PhO CH₃ CH₃ CH₃ OH S B768 PhS CH₃ CH₃ CH₃ OH S B769 PhSO CH₃ CH₃ CH₃ OH S B770 PhSO₂ CH₃ CH₃ CH₃ OH S B771 CN CH₃ CH₃ CH₃ OH S B772 CH₃CH₂ CH₃CH₂ H H OH S B773 CH₃CH₂CH₂ CH₃CH₂ H H OH S B774 (CH₃)₂CH CH₃CH₂ H H OH S B775 (CH₃)₃C CH₃CH₂ H H OH S B776 CH₃S CH₃CH₂ H H OH S B777 CH₃SO CH₃CH₂ H H OH S B778 CH₃SO₂ CH₃CH₂ H H OH S B779 Ph CH₃CH₂ H H OH S B780 CH₃O CH₃CH₂ H H OH S B781 CH₃OC(O) CH₃CH₂ H H OH S B782 CH₃CH₂OC(O) CH₃CH₂ H H OH S B783 CH₂═CHCH₂ CH₃CH₂ H H OH S B784 HCCCH₂ CH₃CH₂ H H OH S B785 CF₃ CH₃CH₂ H H OH S B786 (CH₃)₂NSO₂ CH₃CH₂ H H OH S B787 (CH₃)₂N CH₃CH₂ H H OH S B788 PhO CH₃CH₂ H H OH S B789 PhS CH₃CH₂ H H OH S B790 PhSO CH₃CH₂ H H OH S B791 PhSO₂ CH₃CH₂ H H OH S B792 CN CH₃CH₂ H H OH S B793 H H H H OH SO₂ B794 CH₃ H H H OH SO₂ B795 CH₃CH₂ H H H OH SO₂ B796 CH₃CH₂CH₂ H H H OH SO₂ B797 (CH₃)₂CH H H H OH SO₂ B798 (CH₃)₃C H H H OH SO₂ B799 CH₃S H H H OH SO₂ B800 CH₃SO H H H OH SO₂ B801 CH₃SO₂ H H H OH SO₂ B802 Ph H H H OH SO₂ B803 CH₃O H H H OH SO₂ B804 CH₃OC(O) H H H OH SO₂ B805 CH₃CH₂OC(O) H H H OH SO₂ B806 CH₂═CHCH₂ H H H OH SO₂ B807 HCCCH₂ H H H OH SO₂ B808 CF₃ H H H OH SO₂ B809 (CH₃)₂NSO₂ H H H OH SO₂ B810 (CH₃)₂N H H H OH SO₂ B811 PhO H H H OH SO₂ B812 PhS H H H OH SO₂ B813 PhSO H H H OH SO₂ B814 PhSO₂ H H H OH SO₂ B815 CN H H H OH SO₂ B816 CH₃ CH₃ H H OH SO₂ B817 CH₃CH₂ CH₃ H H OH SO₂ B818 CH₃CH₂CH₂ CH₃ H H OH SO₂ B819 (CH₃)₂CH CH₃ H H OH SO₂ B820 (CH₃)₃C CH₃ H H OH SO₂ B821 CH₃S CH₃ H H OH SO₂ B822 CH₃SO CH₃ H H OH SO₂ B823 CH₃SO₂ CH₃ H H OH SO₂ B824 Ph CH₃ H H OH SO₂ B825 CH₃O CH₃ H H OH SO₂ B826 CH₃OC(O) CH₃ H H OH SO₂ B827 CH₃CH₂OC(O) CH₃ H H OH SO₂ B828 CH₂═CHCH₂ CH₃ H H OH SO₂ B829 HCCCH₂ CH₃ H H OH SO₂ B830 CF₃ CH₃ H H OH SO₂ B831 (CH₃)₂NSO₂ CH₃ H H OH SO₂ B832 (CH₃)₂N CH₃ H H OH SO₂ B833 PhO CH₃ H H OH SO₂ B834 PhS CH₃ H H OH SO₂ B835 PhSO CH₃ H H OH SO₂ B836 PhSO₂ CH₃ H H OH SO₂ B837 CN CH₃ H H OH SO₂ B838 CH₃ H CH₃ H OH SO₂ B839 CH₃CH₂ H CH₃ H OH SO₂ B840 CH₃CH₂CH₂ H CH₃ H OH SO₂ B841 (CH₃)₂CH H CH₃ H OH SO₂ B842 (CH₃)₃C H CH₃ H OH SO₂ B843 CH₃S H CH₃ H OH SO₂ B844 CH₃SO H CH₃ H OH SO₂ B845 CH₃SO₂ H CH₃ H OH SO₂ B846 Ph H CH₃ H OH SO₂ B847 CH₃O H CH₃ H OH SO₂ B848 CH₃OC(O) H OH₃ H OH SO₂ B849 CH₃CH₂OC(O) H CH₃ H OH SO₂ B850 CH₂═CHCH₂ H CH₃ H OH SO₂ B851 HCCCH₂ H CH₃ H OH SO₂ B852 CF₃ H CH₃ H OH SO₂ B853 (CH₃)₂NSO₂ H CH₃ H OH SO₂ B854 (CH₃)₂N H CH₃ H OH SO₂ B855 PhO H CH₃ H OH SO₂ B856 PhS H CH₃ H OH SO₂ B857 PbSO H CH₃ H OH SO₂ B858 PhSO₂ H CH₃ H OH SO₂ B859 CN H CH₃ H OH SO₂ B860 CH₃ CH₃ CH₃ H OH SO₂ B861 CH₃CH₂ CH₃ CH₃ H OH SO₂ B862 CH₃CH₂CH₂ CH₃ CH₃ H OH SO₂ B863 (CH₃)₂CH CH₃ CH₃ H OH SO₂ B864 (CH₃)₃C CH₃ CH₃ H OH SO₂ B865 CH₃S CH₃ CH₃ H OH SO₂ B866 CH₃SO CH₃ CH₃ H OH BO₂ B867 CH₃SO₂ CH₃ CH₃ H OH SO₂ B868 Ph CH₃ CH₃ H OH SO₂ B869 CH₃O CH₃ CH₃ H OH SO₂ B870 CH₃OC(O) CH₃ CH₃ H OH SO₂ B871 CH₃CH₂OC(O) CH₃ CH₃ H OH SO₂ B872 CH₂═CHCH₂ CH₃ CH₃ H OH SO₂ B873 HCCCH₂ CH₃ CH₃ H OH SO₂ B874 CF₃ CH₃ CH₃ H OH SO₂ B875 (CH₃)₂NSO₂ CH₃ CH₃ H OH SO₂ B876 (CH₃)₂N CH₃ CH₃ H OH SO₂ B877 PhO CH₃ CH₃ H OH SO₂ B878 PhS CH₃ CH₃ H OH SO₂ B879 PhSO CH₃ CH₃ H OH SO₂ B880 PhSO₂ CH₃ CH₃ H OH SO₂ B881 CN CH₃ CH₃ H OH SO₂ B882 CH₃ CH₃ CH₃ CH₃ OH SO₂ B883 CH₃CH₂ CH₃ CH₃ CH₃ OH SO₂ B884 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH SO₂ B885 (CH₃)₂CH CH₃ CH₃ CH₃ OH SO₂ B886 (CH₃)₃C CH₃ CH₃ CH₃ OH SO₂ B887 CH₃S CH₃ CH₃ CH₃ OH SO₂ B888 CH₃SO CH₃ CH₃ CH₃ OH SO₂ B889 CH₃SO₂ CH₃ CH₃ CH₃ OH SO₂ B890 Ph CH₃ CH₃ CH₃ OH SO₂ B891 CH₃O CH₃ CH₃ CH₃ OH SO₂ B892 CH₃OC(O) CH₃ CH₃ CH₃ OH SO₂ B893 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH SO₂ B894 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH SO₂ B895 HCCCH₂ CH₃ CH₃ CH₃ OH SO₂ B896 CF₃ CH₃ CH₃ CH₃ OH SO₂ B897 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH SO₂ B898 (CH₃)₂N CH₃ CH₃ CH₃ OH SO₂ B899 PhO CH₃ CH₃ CH₃ OH SO₂ B900 PhS CH₃ CH₃ CH₃ OH SO₂ B901 PhSO CH₃ CH₃ CH₃ OH SO₂ B902 PhSO₂ CH₃ CH₃ CH₃ OH SO₂ B903 CN CH₃ CH₃ CH₃ OH SO₂ B904 CH₃CH₂ CH₃CH₂ H H OH SO₂ B905 CH₃CH₂CH₂ CH₃CH₂ H H OH SO₂ B906 (CH₃)₂CH CH₃CH₂ H H OH SO₂ B907 (CH₃)₃C CH₃CH₂ H H OH SO₂ B908 CH₃S CH₃CH₂ H H OH SO₂ B909 CH₃SO CH₃CH₂ H H OH SO₂ B910 CH₃SO₂ CH₃CH₂ H H OH SO₂ B911 Ph CH₃CH₂ H H OH SO₂ B912 CH₃O CH₃CH₂ H H OH SO₂ B913 CH₃OC(O) CH₃CH₂ H H OH SO₂ B914 CH₃CH₂OC(O) CH₃CH₂ H H OH SO₂ B915 CH₂═CHCH₂ CH₃CH₂ H H OH SO₂ B916 HCCCH₂ CH₃CH₂ H H OH SO₂ B917 CF₃ CH₃CH₂ H H OH SO₂ B918 (CH₃)₂NSO₂ CH₃CH₂ H H OH SO₂ B919 (CH₃)₂N CH₃CH₂ H H OH SO₂ B920 PhO CH₃CH₂ H H OH SO₂ B921 PhS CH₃CH₂ H H OH SO₂ B922 PhSO CH₃CH₂ H H OH SO₂ B923 PhSO₂ CH₃CH₂ H H OH SO₂ B924 CN CH₃CH₂ H H OH SO₂ B925 H H H H OH CHC(O)OCH₂CH₃ B926 CH₃ H H H OH CHC(O)OCH₂CH₃ B927 CH₃CH₂ H H H OH CHC(O)OCH₂CH₃ B928 CH₃CH₂CH₂ H H H OH CHC(O)OCH₂CH₃ B929 (CH₃)₂CH H H H OH CHC(O)OCH₂CH₃ B930 (CH₃)₃C H H H OH CHC(O)OCH₂CH₃ B931 CH₃S H H H OH CHC(O)OCH₂CH₃ B932 CH₃SO H H H OH CHC(O)OCH₂CH₃ B933 CH₃SO₂ H H H OH CHC(O)OCH₂CH₃ B934 Ph H H H OH CHC(O)OCH₂CH₃ B935 CH₃O H H H OH CHC(O)OCH₂CH₃ B936 CH₃OC(O) H H H OH CHC(O)OCH₂CH₃ B937 CH₃CH₂OC(O) H H H OH CHC(O)OCH₂CH₃ B938 CH₂═CHCH₂ H H H OH CHC(O)OCH₂CH₃ B939 HCCCH₂ H H H OH CHC(O)OCH₂CH₃ B940 CF₃ H H H OH CHC(O)OCH₂CH₃ B941 (CH₃)₂NSO₂ H H H OH CHC(O)OCH₂CH₃ B942 (CH₃)₂N H H H OH CHC(O)OCH₂CH₃ B943 PhO H H H OH CHC(O)OCH₂CH₃ B944 PhS H H H OH CHC(O)OCH₂CH₃ B945 PhSO H H H OH CHC(O)OCH₂CH₃ B946 PhSO₂ H H H OH CHC(O)OCH₂CH₃ B947 CN H H H OH CHC(O)OCH₂CH₃ B948 CH₃ CH₃ H H OH CHC(O)OCH₂CH₃ B949 CH₃CH₂ CH₃ H H OH CHC(O)OCH₂CH₃ B950 CH₃CH₂CH₂ CH₃ H H OH CHC(O)OCH₂CH₃ B951 (CH₃)₂CH CH₃ H H OH CHC(O)OCH₂CH₃ B952 (CH₃)₃C CH₃ H H OH CHC(O)OCH₂CH₃ B953 CH₃S CH₃ H H OH CHC(O)OCH₂CH₃ B954 CH₃SO CH₃ H H OH CHC(O)OCH₂CH₃ B955 CH₃SO₂ CH₃ H H OH CHC(O)OCH₂CH₃ B956 Ph CH₃ H H OH CHC(O)OCH₂CH₃ B957 CH₃O CH₃ H H OH CHC(O)OCH₂CH₃ B958 CH₃OC(O) CH₃ H H OH CHC(O)OCH₂CH₃ B959 CH₃CH₂OC(O) CH₃ H H OH CHC(O)OCH₂CH₃ B960 CH₂═CHCH₂ CH₃ H H OH CHC(O)OCH₂CH₃ B961 HCCCH₂ CH₃ H H OH CHC(O)OCH₂CH₃ B962 CF₃ CH₃ H H OH CHC(O)OCH₂CH₃ B963 (CH₃)₂NSO₂ CH₃ H H OH CHC(O)OCH₂CH₃ B964 (CH₃)₂N CH₃ H H OH CHC(O)OCH₂CH₃ B965 PhO CH₃ H H OH CHC(O)OCH₂CH₃ B966 PhS CH₃ H H OH CHC(O)OCH₂CH₃ B967 PhSO CH₃ H H OH CHC(O)OCH₂CH₃ B968 PhSO₂ CH₃ H H OH CHC(O)OCH₂CH₃ B969 CN CH₃ H H OH CHC(O)OCH₂CH₃ B970 CH₃ H CH₃ H OH CHC(O)OCH₂CH₃ B971 CH₃CH₂ H CH₃ H OH CHC(O)OCH₂CH₃ B972 CH₃CH₂CH₂ H CH₃ H OH CHC(O)OCH₂CH₃ B973 (CH₃)₂CH H CH₃ H OH CHC(O)OCH₂CH₃ B974 (CH₃)₃C H CH₃ H OH CHC(O)OCH₂CH₃ B975 CH₃S H CH₃ H OH CHC(O)OCH₂CH₃ B976 CH₃SO H CH₃ H OH CHC(O)OCH₂CH₃ B977 CH₃SO₂ H CH₃ H OH CHC(O)OCH₂CH₃ B978 Ph H CH₃ H OH CHC(O)OCH₂CH₃ B979 CH₃O H CH₃ H OH CHC(O)OCH₂CH₃ B980 CH₃OC(O) H CH₃ H OH CHC(O)OCH₂CH₃ B981 CH₃CH₂OC(O) H CH₃ H OH CHC(O)OCH₂CH₃ B982 CH₂═CHCH₂ H CH₃ H OH CHC(O)OCH₂CH₃ B983 HCCCH₂ H CH₃ H OH CHC(O)OCH₂CH₃ B984 CF₃ H CH₃ H OH CHC(O)OCH₂CH₃ B985 (CH₃)₂NSO₂ H CH₃ H OH CHC(O)OCH₂CH₃ B986 (CH₃)₂N H CH₃ H OH CHC(O)OCH₂CH₃ B987 PhO H CH₃ H OH CHC(O)OCH₂OH₃ B988 PhS H CH₃ H OH CHC(O)OCH₂CH₃ B989 PhSO H CH₃ H OH CHC(O)OCH₂CH₃ B990 PhSO₂ H CH₃ H OH CHC(O)OCH₂CH₃ B991 CN H CH₃ H OH CHC(O)OCH₂CH₃ B992 CH₃ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B993 CH₃CH₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B994 CH₃CH₂CH₂ CH₃ CH₃ H OH CHC(O)CCH₂CH₃ B995 (CH₃)₂CH CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B996 (CH₃)₃C CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B997 CH₃S CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B998 CH₃SO CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B999 CH₃SO₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1000 Ph CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1001 CH₃O CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1002 CH₃OC(O) CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1003 CH₃CH₂OC(O) CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1004 CH₂═CHCH₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1005 HCCCH₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1006 CF₃ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1007 (CH₃)₂NSO₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1008 (CH₃)₂N CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1009 PhO CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1010 PhS CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1011 PhSO CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1012 PhSO₂ CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1013 CN CH₃ CH₃ H OH CHC(O)OCH₂CH₃ B1014 CH₃ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1015 CH₃CH₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1016 CH₃CH₂CH₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1017 (CH₃)₂CH CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1018 (CH₃)₃C CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1019 CH₃S CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1020 CH₃SO CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1021 CH₃SO₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1022 Ph CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1023 CH₃O CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1024 CH₃OC(O) CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1025 CH₃CH₂OC(O) CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1026 CH₂═CHCH₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1027 HCCCH₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1028 CF₃ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1029 (CH₃)₂NSO₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1030 (CH₃)₂N CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1031 PhO CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1032 PhS CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1033 PhSO CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1034 PhSO₂ CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1035 CN CH₃ CH₃ CH₃ OH CHC(O)OCH₂CH₃ B1036 CH₃CH₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1037 CH₃CH₂CH₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1038 (CH₃)₂CH CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1039 (CH₃)₃C CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1040 CH₃S CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1041 CH₃SO CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1042 CH₃SO₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1043 Ph CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1044 CH₃O CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1045 CH₃OC(O) CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1046 CH₃CH₂OC(O) CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1047 CH₂═CHCH₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1048 HCCCH₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1049 CF₃ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1050 (CH₃)₂NSO₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1051 (CH₃)₂N CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1052 PhO CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1053 PhS CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1054 PhSO CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1055 PhSO₂ CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1056 CN CH₃CH₂ H H OH CHC(O)OCH₂CH₃ B1057 CH₃OC(O) H H H OH CHPh B1058 H H H H OH CHPh B1059 H H H H OH CH(CH₂CH₃) B1060 H H H H OH CH(CH₂CH₂CH₃) B1061 H H H H OH CH(CH(CH₃)₂) B1062 H H H H OH CH(C(CH₃)₃) B1063 H H H H OH C(CH₃)₂ B1064 H H H H OH CH(CF₃) B1065 CH₃OC(O) H H H OH C(CH₃)(CF₃) B1066 H H H H OH C(CH₃)(CF₃) B1067 CH₃OC(O) CH₃O H H OH CH₂ B1068 H CH₃O H H OH CH₂ B1069 CH₃O CH₃OC(O) H CH₃ OH CH₂ B1070 CH₃O H CH₃ H OH CH₂ B1071 Cl H H H OH CH₂ B1072 F H H H OH CH₂ B1073 H H H H OH CH(OCH₃)₂ B1074 H H H H OH CH₂OSO₂CH₃ B1075 CH₃ CH₃ CH₃ CH₃ OH S(O) B1076 ClCH₂CH₂ H H H OH CH₂ B1077 HO(CH₂)₂ H H H OH CH₂ B1078 MsO(CH₂)₂ H H H OH CH₂ B1079 HOCH(CH₃)CH₂ H H H OH CH₂ B1080 MsOCH(CH₃)CH₂ H H H OH CH₂ B1081 (CH₃)₂CH H CH₃ CH₃ OH CH₂ B1082 HCCCH₂ H CH₃ CH₃ OH CH₂ B1083 H₂C═CCH₂ H CH₃ CH₃ OH CH₂ B1084 H₂C═C(CH₃) H H H OH CHCH₃ B1085 H H H H OH CHCONHCH₂Ph B1086 H H H H OH

B1087 CH₃OC(O) CH₃ H H OH C(CH₃)₂ B1088 H H H H OH

B1089 CH₃CH₂ H CH₃ CH₃ OH CH₂ B1090 CH₃OC(O) H H H OH CF₃CH₂CH₂ B1091 CH₃CH₂S CH₃CH₂ CH₃ H OH CH₂ B1092 CH₃S Ph CH₃ H OH CH₂ B1093 CH₃CH₂ CH₃CH₂ CH₃ H OH CH₂ B1094 CH₃OC(O) H H H OH C(CH₃)₂ B1095 CH₃ H H H OH C(CH₃)₂ B1096 H H H H OH NCOCH₂SCH₃ B1097

H H H OH CH₂ B1098 1,1-dimethylvinyl H H H OH CH₂ B1099

H H H OH CH₂ B1100 H H H H —ONH+(CH₂CH₃)₃ CH₂ B1101 H H H H —ONH+(CH₂CH₃)₃ CH(CH₃) B1102 H H H H PhS CH₂ B1103 H H H H PhSO CH₂ B1104 H H H H PhSO₂ CH₂ B1105 CH₃ CH₃ CH₃ CH₃ Cl C═O B1106 H H H H OH CHCH₂CH(CH₃)₂ B1107 CH₃ CH₃ CH₃ CH₃ CH₃C(O)O C═O B1108 CH₃OC(O)CH₂ H H H OH CH₂ B1109 CH₃OC(O)CH₂ CH₃ H H OH CH₂ B1110 CH₃OC(O)CH₂ CH₃ CH₃ H OH CH₂ B1111 CH₃OC(O)CH₂ CH₃ CH₃ CH₃ OH CH₂ B1112 CH₃OC(O)CH₂ H CH₃ CH₃ OH CH₂ B1113 CH₃CC(O)CH₂ H H H OH CH(CH₃) B1114 CH₃OC(O)CH₂ CH₃ H H OH CH(CH₃) B1115 CH₃OC(O)CH₂ CH₃ CH₃ H OH CH(CH₃) B1116 CH₃OC(O)CH₂ CH₃ CH₃ CH₃ OH CH(CH₃) B1117 CH₃OC(O)CH₂ H CH₃ CH₃ OH CH(CH₃) B1118 CH₃OC(O)CH₂ H H H OH C(CH₃)₂ B1119 CH₃CC(O)CH₂ CH₃ H H OH C(CH₃)₂ B1120 CH₃OC(O)CH₂ CH₃ CH₃ H OH C(CH₃)₂ B1121 CH₃OC(O)CH₂ CH₃ CH₃ CH₃ OH C(CH₃)₂ B1122 CH₃OC(O)CH₂ H CH₃ CH₃ OH C(CH₃)₂ B1123 CH₃CH₂OC(O)CH₂ H H H OH CH₂ B1124 CH₃CH₂OC(O)CH₂ CH₃ H H OH CH₂ B1125 CH₃CH₂OC(O)CH₂ CH₃ CH₃ H OH CH₂ B1126 CH₃CH₂OC(O)CH₂ CH₃ CH₃ CH₃ OH CH₂ B1127 CH₃CH₂OC(O)CH₂ H CH₃ CH₃ OH CH₂ B1128 CH₃CH₂OC(O)CH₂ H H H OH CH(CH₃) B1129 CH₃CH₂OC(O)CH₂ CH₃ H H OH CH(CH₃) B1130 CH₃CH₂OC(O)CH₂ CH₃ CH₃ H OH CH(CH₃) B1131 CH₃CH₂OC(O)CH₂ CH₃ CH₃ CH₃ OH CH(CH₃) B1132 CH₃CH₂OC(O)CH₂ H CH₃ CH₃ OH CH(CH₃) B1133 CH₃CH₂OC(O)CH₂ H H H OH C(CH₃)₂ B1134 CH₃CH₂OC(O)CH₂ CH₃ H H OH C(CH₃)₂ B1135 CH₃CH₂OC(O)CH₂ CH₃ CH₃ H OH C(CH₃)₂ B1136 CH₃CH₂OC(O)CH₂ CH₃ CH₃ CH₃ OH C(CH₃)₂ B1137 CH₃CH₂OC(O)CH₂ H CH₃ CH₃ OH C(CH₃)₂ B1138

CH₃ H H OH CH₂ B1139 CH₃SCH₂ H H H OH CH₂ B1140 CH₃SCH₂ CH₃ H H OH CH₂ B1141 CH₃SCH₂ CH₃ CH₃ H OH CH₂ B1142 CH₃SCH₂ CH₃ CH₃ CH₃ OH CH₂ B1143 CH₃SCH₂ H CH₃ CH₃ OH CH₂ B1144 CH₃SOCH₂ H H H OH CH₂ B1145 CH₃SOCH₂ CH₃ H H OH CH₂ B1146 CH₃SOCH₂ CH₃ CH₃ H OH CH₂ B1147 CH₃SOCH₂ CH₃ CH₃ CH₃ OH CH₂ B1148 CH₃SOCH₂ H CH₃ CH₃ OH CH₂ B1149 CH₃SO₂CH₂ H H H OH CH₂ B1150 CH₃SO₂CH₂ CH₃ H H OH CH₂ B1151 CH₃SO₂CH₂ CH₃ CH₃ H OH CH₂ B1152 CH₃SO₂CH₂ CH₃ CH₃ CH₃ OH CH₂ B1153 CH₃SO₂CH₂ H CH₃ CH₃ OH CH₂ B1154 HOCH₂ H H H OH CH₂ B1155 HOCH₂ CH₃ H H OH CH₂ B1156 HOCH₂ CH₃ CH₃ H OH CH₂ B1157 HOCH₂ CH₃ CH₃ CH₃ OH CH₂ B1158 HOCH₂ H CH₃ CH₃ OH CH₂ B1159 NCCH₂ H H H OH CH₂ B1160 NCCH₂ CH₃ H H OH CH₂ B1161 NCCH₂ CH₃ CH₃ H OH CH₂ B1162 NCCH₂ CH₃ CH₃ CH₃ OH CH₂ B1163 NCCH₂ H CH₃ CH₃ OH CH₂ B1164 CH₃C(O)OCH₂ H H H OH CH₂ B1165 CH₃C(O)OCH₂ CH₃ H H OH CH₂ B1166 CH₃C(O)OCH₂ CH₃ CH₃ H OH CH₂ B1167 CH₃C(O)OCH₂ CH₃ CH₃ CH₃ OH CH₂ B1168 CH₃C(O)OCH₂ H CH₃ CH₃ OH CH₂ B1169 CH₃OCH₂ H H H OH CH₂ B1170 CH₃OCH₂ CH₃ H H OH CH₂ B1171 CH₃OCH₂ CH₃ CH₃ H OH CH₂ B1172 CH₃OCH₂ CH₃ CH₃ CH₃ OH CH₂ B1173 CH₃OCH₂ H CH₃ CH₃ OH CH₂ B1174 PhCH₂ H H H OH CH₂ B1175 PhCH₂ CH₃ H H OH CH₂ B1176 PhCH₂ CH₃ CH₃ H OH CH₂ B1177 PhCH₂ CH₃ CH₃ CH₃ OH CH₂ B1178 PhCH₂ H CH₃ CH₃ OH CH₂ B1179 H H H H O—K+ CH₂ B1180 H H H H S(CH₂)₇CH₃ CH₂ B1181 H H H H S(CH₂)₇CH₃ CH₂ B1182 H H H H SO(CH₂)₇CH₃ CH₂ B1183 H H H H SO₂(CH₂)₇CH₃ CH₂ B1184 H H H H NHSO₂CH₃ CH₂ B1185 H H H H NH(CO)S(CH₂)₇CH₃ CH₂ B1186 H H H H Cl CH₂ B1187 H H H H NH₂ CH₂ B1188 H H H H OC(O)C(CH₃)₃ CH₂ B1189 H H H H OC(O)CH₃ CH₂ B1190 H H H H OC(O)Ph CH₂ B1191 H H H H OC(O)-cyclopropyl CH₂ B1192 H H H H OC(O)CH₂CH₃ CH₂ B1193 H H H H OC(O)CH═CH₂ CH₂ B1194 H H H H OC(O)CH═CHCH₃ CH₂ B1195 H H H H OC(O)SCH₃ CH₂ B1196 H H H H OC(O)S(CH₂)₇CH₃ CH₂ B1197 H H H H OC(O)OCH₂CH₃ CH₂ B1198 H H H H OC(O)N(CH₂CH₃)₂ CH₂ B1199 H H H H S-(4-Cl-phenyl) CH₂ B1200 H H H H SO-(4-Cl-phenyl) CH₂ B1201 H H H H SO₂-(4-Cl-phenyl) CH₂ B1202 H H H H S-(4-CF₃-phenyl) CH₂ B1203 H H H H SO-(4-CF₃-phenyl) CH₂ B1204 H H H H SO₂-(4-CF₃-phenyl) CH₂ B1205 H H H H S-(4-NO₂-phenyl) CH₂ B1206 H H H H SO-(4-NO₂-phenyl) CH₂ B1207 H H H H SO₂-(4-NO₂-phenyl) CH₂ B1208 H H H H

CH₂ B1209 H H H H

CH₂ B1210 H H H H

CH₂ B1211 H H H H

CH₂ B1212 H H H H

CH₂ B1179 CH₃ CH₃ H H O—K+ CH₂ B1180 CH₃ CH₃ H H S(CH₂)₇CH₃ CH₂ B1181 CH₃ CH₃ H H S(CH₂)₇CH₃ CH₂ B1182 CH₃ CH₃ H H SO(CH₂)₇CH₃ CH₂ B1183 CH₃ CH₃ H H SO₂(CH₂)₇CH₃ CH₂ B1184 CH₃ CH₃ H H NHSO₂CH₃ CH₂ B1185 CH₃ CH₃ H H NH(CO)S(CH₂)₇CH₃ CH₂ B1186 CH₃ CH₃ H H Cl CH₂ B1187 CH₃ CH₃ H H NH₂ CH₂ B1188 CH₃ CH₃ H H OC(O)C(CH₃)₃ CH₂ B1189 CH₃ CH₃ H H OC(O)CH₃ CH₂ B1190 CH₃ CH₃ H H OC(O)Ph CH₂ B1191 CH₃ CH₃ H H OC(O)-cyclopropyl CH₂ B1192 CH₃ CH₃ H H OC(O)CH₂CH₃ CH₂ B1193 CH₃ CH₃ H H OC(O)CH═CH₂ CH₂ B1194 CH₃ CH₃ H H OC(O)CH═CHCH₃ CH₂ B1195 CH₃ CH₃ H H OC(O)SCH₃ CH₂ B1196 CH₃ CH₃ H H OC(O)S(CH₂)₇CH₃ CH₂ B1197 CH₃ CH₃ H H OC(O)OCH₂CH₃ CH₂ B1198 CH₃ CH₃ H H OC(O)N(CH₂CH₃)₂ CH₂ B1199 CH₃ CH₃ H H S-(4-Cl-phenyl) CH₂ B1200 CH₃ CH₃ H H SO-(4-Cl-phenyl) CH₂ B1201 CH₃ CH₃ H H SO₂-(4-Cl-phenyl) CH₂ B1202 CH₃ CH₃ H H S-(4-CF₃-pheny1) CH₂ B1203 CH₃ CH₃ H H SO-(4-CF₃-phenyl) CH₂ B1204 CH₃ CH₃ H H SO₂-(4-CF₃-pheny1) CH₂ B1205 CH₃ CH₃ H H S-(4-NO₂-phenyl) CH₂ B1206 CH₃ CH₃ H H SO-(4-NO₂-phenyl) CH₂ B1207 CH₃ CH₃ H H SO₂-(4-NO₂-phenyl) CH₂ B1208 CH₃ CH₃ H H

CH₂ B1209 CH₃ CH₃ H H

CH₂ B1210 CH₃ CH₃ H H

CH₂ B1211 CH₃ CH₃ H H

CH₂ B1212 CH₃ CH₃ H H

CH₂ B1213 H H H H OH —CH₂CH₂— B1214 CH₃ H H H OH —CH₂CH₂— B1215 CH₃ CH₃ H H OH —CH₂CH₂— B1216 CH₃ CH₃ CH₃ H OH —CH₂CH₂— B1217 CH₃ CH₃ CH₃ CH₃ OH —CH₂CH₂—

In Table 3 which follows, Q is Q₂

and Q₂ the radicals C which follow:

TABLE 3 Radicals C: Radical R₆ R₇ R₁₆ R₁₀ p W C1 H H H OH 1 CH₂ C2 CH₃ H H OH 1 CH₂ C3 CH₃CH₂ H H OH 1 CH₂ C4 CH₃CH₂CH₂ H H OH 1 CH₂ C5 (CH₃)₂CH H H OH 1 CH₂ C6 (CH₃)₃C H H OH 1 CH₂ C7 CH₃S H H OH 1 CH₂ C8 CH₃SO H H OH 1 CH₂ C9 CH₃SO₂ H H OH 1 CH₂ C10 Ph H H OH 1 CH₂ C11 CH₃O H H OH 1 CH₂ C12 CH₃OC(O) H H OH 1 CH₂ C13 CH₃CH₂OC(O) H H OH 1 CH₂ C14 CH₂═CHCH₂ H H OH 1 CH₂ C15 HCCCH₂ H H OH 1 CH₂ C16 CF₃ H H OH 1 CH₂ C17 (CH₃)₂NSO₂ H H OH 1 CH₂ C18 (CH₃)_(2N) H H OH 1 CH₂ C19 PhO H H OH 1 CH₂ C20 PhS H H OH 1 CH₂ C21 PhSO H H OH 1 CH₂ C22 PhSO₂ H H OH 1 CH₂ C23 CN H H OH 1 CH₂ C24 CH₃ CH₃ H OH 1 CH₂ C25 CH₃CH₂ CH₃ H OH 1 CH₂ C26 CH₃CH₂CH₂ CH₃ H OH 1 CH₂ C27 (CH₃)₂CH CH₃ H OH 1 CH₂ C28 (CH₃)₃C CH₃ H OH 1 CH₂ C29 CH₃S CH₃ H OH 1 CH₂ C30 CH₃SO CH₃ H OH 1 CH₂ C31 CH₃SO₂ CH₃ H OH 1 CH₂ C32 Ph CH₃ H OH 1 CH₂ C33 CH₃O CH₃ H OH 1 CH₂ C34 CH₃OC(O) CH₃ H OH 1 CH₂ C35 CH₃CH₂OC(O) CH₃ H OH 1 CH₂ C36 CH₂═CHCH₂ CH₃ H OH 1 CH₂ C37 HCCCH₂ CH₃ H OH 1 CH₂ C38 CF₃ CH₃ H OH 1 CH₂ C39 (CH₃)₂NSO₂ CH₃ H OH 1 CH₂ C40 (CH₃)₂N CH₃ H OH 1 CH₂ C41 PhO CH₃ H OH 1 CH₂ C42 PhS CH₃ H OH 1 CH₂ C43 PhSO CH₃ H OH 1 CH₂ C44 PhSO₂ CH₃ H OH 1 CH₂ C45 CN CH₃ H OH 1 CH₂ C46 H H H OH 4 CH₂ C47 CH₃ H H OH 4 CH₂ C48 CH₃CH₂ H H OH 4 CH₂ C49 CH₃CH₂CH₂ H H OH 4 CH₂ C50 (CH₃)₂CH H H OH 4 CH₂ C51 (CH₃)₃C H H OH 4 CH₂ C52 CH₃S H H OH 4 CH₂ C53 CH₃SO H H OH 4 CH₂ C54 CH₃SO₂ H H OH 4 CH₂ C55 Ph H H OH 4 CH₂ C56 CH₃O H H OH 4 CH₂ C57 CH₃OC(O) H H OH 4 CH₂ C58 CH₃CH₂OC(O) H H OH 4 CH₂ C59 CH₂═CHCH₂ H H OH 4 CH₂ C60 HCCCH₂ H H OH 4 CH₂ C61 CF₃ H H OH 4 CH₂ C62 (CH₃)₂NSO₂ H H OH 4 CH₂ C63 (CH₃)₂N H H OH 4 CH₂ C64 PhO H H OH 4 CH₂ C65 PhS H H OH 4 CH₂ C66 PhSO H H OH 4 CH₂ C67 PhSO₂ H H OH 4 CH₂ C68 CN H H OH 4 CH₂ C69 CH₃ CH₃ H OH 4 CH₂ C70 CH₃CH₂ CH₃ H OH 4 CH₂ C71 CH₃CH₂CH₂ CH₃ H OH 4 CH₂ C72 (CH₃)₂CH CH₃ H OH 4 CH₂ C73 (CH₃)₃C CH₃ H OH 4 CH₂ C74 CH₃S CH₃ H OH 4 CH₂ C75 CH₃SO CH₃ H OH 4 CH₂ C76 CH₃SO₂ CH₃ H OH 4 CH₂ C77 Ph CH₃ H OH 4 CH₂ C78 CH₃O CH₃ H OH 4 CH₂ C79 CH₃OC(O) CH₃ H OH 4 CH₂ C80 CH₃CH₂OC(O) CH₃ H OH 4 CH₂ C81 CH₂═CHCH₂ CH₃ H OH 4 CH₂ C82 HCCCH₂ CH₃ H OH 4 CH₂ C83 CF₃ CH₃ H OH 4 CH₂ C84 (CH₃)₂NSO₂ CH₃ H OH 4 CH₂ C85 (CH₃)₂N CH₃ H OH 4 CH₂ C86 PhO CH₃ H OH 4 CH₂ C87 PhS CH₃ H OH 4 CH₂ C88 PhSO CH₃ H OH 4 CH₂ C89 PhSO₂ CH₃ H OH 4 CH₂ C90 CN CH₃ H OH 4 CH₂ C91 H H H OH 3 CH₂ C92 CH₃ H H OH 3 CH₂ C93 CH₃CH₂ H H OH 3 CH₂ C94 CH₃CH₂CH₂ H H OH 3 CH₂ C95 (CH₃)₂CH H H OH 3 CH₂ C96 (CH₃)₃C H H OH 3 CH₂ C97 CH₃S H H OH 3 CH₂ C98 CH₃SO H H OH 3 CH₂ C99 CH₃SO₂ H H OH 3 CH₂ C100 Ph H H OH 3 CH₂ C101 CH₃O H H OH 3 CH₂ C102 CH₃OC(O) H H OH 3 CH₂ C103 CH₃CH₂OC(O) H H OH 3 CH₂ C104 CH₂═CHCH₂ H H OH 3 CH₂ C105 HCCCH₂ H H OH 3 CH₂ C106 CF₃ H H OH 3 CH₂ C107 (CH₃)₂NSO₂ H H OH 3 CH₂ C108 (CH₃)₂N H H OH 3 CH₂ C109 PhO H H OH 3 CH₂ C110 PhS H H OH 3 CH₂ C111 PhSO H H OH 3 CH₂ C112 PhSO₂ H H OH 3 CH₂ C113 CN H H OH 3 CH₂ C114 CH₃ CH₃ H OH 3 CH₂ C115 CH₃CH₂ CH₃ H OH 3 CH₂ C116 CH₃CH₂CH₂ CH₃ H OH 3 CH₂ C117 (CH₃)₂CH CH₃ H OH 3 CH₂ C118 (CH₃)₃C CH₃ H OH 3 CH₂ C119 CH₃S CH₃ H OH 3 CH₂ C120 CH₃SO CH₃ H OH 3 CH₂ C121 CH₃SO₂ CH₃ H OH 3 CH₂ C122 Ph CH₃ H OH 3 CH₂ C123 CH₃O CH₃ H OH 3 CH₂ C124 CH₃OC(O) CH₃ H OH 3 CH₂ C125 CH₃CH₂OC(O) CH₃ H OH 3 CH₂ C126 CH₂═CHCH₂ CH₃ H OH 3 CH₂ C127 HCCCH₂ CH₃ H OH 3 CH₂ C128 CF₃ CH₃ H OH 3 CH₂ C129 (CH₃)₂NSO₂ CH₃ H OH 3 CH₂ C130 (CH₃)₂N CH₃ H OH 3 CH₂ C131 PhO CH₃ H OH 3 CH₂ C132 PhS CH₃ H OH 3 CH₂ C133 PhSO CH₃ H OH 3 CH₂ C134 PhSO₂ CH₃ H OH 3 CH₂ C135 CN CH₃ H OH 3 CH₂ C136 CH₃CH₂ CH₃CH₂ H OH 1 CH₂ C137 H H H OH 1 CH(CH₃₎ C138 CH₃ H H OH 1 CH(CH₃₎ C139 CH₃ CH₃ H OH 1 CH(CH₃₎ C140 CH_(2CH) ₃ H H OH 1 CH(CH₃₎ C141 CH_(2CH) ₃ CH₃ H OH 1 CH(CH₃₎ C142 CH₃CH₂ CH₃CH₂ H OH 1 CH(CH₃₎ C143 H H CH₃ OH 1 CH₂ C144 CH₃ CH₃ CH₃ OH 1 CH₂ C145 CH₃CH₂ CH₃CH₂ CH₃ OH 1 CH₂ C146 H H H OH 2 CH₂ C147 CH₃ CH₃ H OH 2 CH₂ C148 CH₃CH₂ CH₃CH₂ H OH 2 CH₂ C149 H H H OH 5 CH₂ C150 CH₃ CH₃ H OH 5 CH₂ C151 CH₃CH₂ CH₃CH₂ H OH 5 CH₂ C152 CH₃ H H OH 2 CH₂

In Table 4 which follows, Q is Q₃

and Q₃ the following radicals D:

TABLE 4 Radicals D: Radical R₆ R₇ R₈ R₁₂ R₁₀ o D1 H H H H OH 2 D2 CH₃ H H H OH 2 D3 CH₃CH₂ H H H OH 2 D4 CH₃CH₂CH₂ H H H OH 2 D5 (CH₃)₂CH H H H OH 2 D6 (CH₃)₃C H H H OH 2 D7 CH₃S H H H OH 2 D8 CH₃SO H H H OH 2 D9 CH₃SO₂ H H H OH 2 D10 Ph H H H OH 2 D11 CH₃O H H H OH 2 D12 CH₂═CHCH₂ H H H OH 2 D13 HCCCH₂ H H H OH 2 D14 CF₃ H H H OH 2 D15 PhO H H H OH 2 D16 PhS H H H OH 2 D17 PhSO H H H OH 2 D18 PhSO₂ H H H OH 2 D19 CH₃ CH₃ H H OH 2 D20 CH₃CH₂ CH₃ H H OH 2 D21 CH₃CH₂CH₂ CH₃ H H OH 2 D22 (CH₃)₂CH CH₃ H H OH 2 D23 (CH₃)₃C CH₃ H H OH 2 D24 CH₃S CH₃ H H OH 2 D25 CH₃SO CH₃ H H OH 2 D26 CH₃SO₂ CH₃ H H OH 2 D27 Ph CH₃ H H OH 2 D28 CH₃O CH₃ H H OH 2 D29 CH₂═CHCH₂ CH₃ H H OH 2 D30 HCCCH₂ CH₃ H H OH 2 D31 CF₃ CH₃ H H OH 2 D32 PhO CH₃ H H OH 2 D33 PhS CH₃ H H OH 2 D34 PhSO CH₃ H H OH 2 D35 PhSO₂ CH₃ H H OH 2 D36 H H H H OH 3 D37 CH₃ H H H OH 3 D38 CH₃CH₂ H H H OH 3 D39 CH₃CH₂CH₂ H H H OH 3 D40 (CH₃)₂CH H H H OH 3 D41 (CH₃)₃C H H H OH 3 D42 CH₃S H H H OH 3 D43 CH₃SO H H H OH 3 D44 CH₃SO₂ H H H OH 3 D45 Ph H H H OH 3 D46 CH₃O H H H OH 3 D47 CH₂═CHCH₂ H H H OH 3 D48 HCCCH₂ H H H OH 3 D49 CF₃ H H H OH 3 D50 PhO H H H OH 3 D51 PhS H H H OH 3 D52 PhSO H H H OH 3 D53 PhSO₂ H H H OH 3 D54 CH₃ CH₃ H H OH 3 D55 CH₃CH₂ CH₃ H H OH 3 D56 CH₃CH₂CH₂ CH₃ H H OH 3 D57 (CH₃)₂CH CH₃ H H OH 3 D58 (CH₃)₃C CH₃ H H OH 3 D59 CH₃S CH₃ H H OH 3 D60 CH₃SO CH₃ H H OH 3 D61 CH₃SO₂ CH₃ H H OH 3 D62 Ph CH₃ H H OH 3 D63 CH₃O CH₃ H H OH 3 D64 CH₂═CHCH₂ CH₃ H H OH 3 D65 HCCCH₂ CH₃ H H OH 3 D66 CF₃ CH₃ H H OH 3 D67 PhO CH₃ H H OH 3 D68 PhS CH₃ H H OH 3 D69 PhSO CH₃ H H OH 3 D70 PhSO₂ CH₃ H H OH 3 D71 H H H H OH 4 D72 CH₃ H H H OH 4 D73 CH₃CH₂ H H H OH 4 D74 CH₃CH₂CH₂ H H H OH 4 D75 (CH₃)₂CH H H H OH 4 D76 (CH₃)₃C H H H OH 4 D77 CH₃S H H H OH 4 D78 CH₃SO H H H OH 4 D79 CH₃SO₂ H H H OH 4 D80 Ph H H H OH 4 D81 CH₃O H H H OH 4 D82 CH₂═CHCH₂ H H H OH 4 D83 HCCCH₂ H H H OH 4 D84 CF₃ H H H OH 4 D85 PhO H H H OH 4 D86 PhS H H H OH 4 D87 PhSO H H H OH 4 D88 PhSO₂ H H H OH 4 D89 CH₃ CH₃ H H OH 4 D90 CH₃CH₂ CH₃ H H OH 4 D91 CH₃CH₂CH₂ CH₃ H H OH 4 D92 (CH₃)₂CH CH₃ H H OH 4 D93 (CH₃)₃C CH₃ H H OH 4 D94 CH₃S CH₃ H H OH 4 D95 CH₃SO CH₃ H H OH 4 D96 CH₃SO₂ CH₃ H H OH 4 D97 Ph CH₃ H H OH 4 D98 CH₃O CH₃ H H OH 4 D99 CH₂═CHCH₂ CH₃ H H OH 4 D100 HCCCH₂ CH₃ H H OH 4 D101 CF₃ CH₃ H H OH 4 D102 PhO CH₃ H H OH 4 D103 PhS CH₃ H H OH 4 D104 PhSO CH₃ H H OH 4 D105 PhSO₂ CH₃ H H OH 4 D106 H H H CH₃ OH 4 D107 H H H CH₃ OH 3 D108 H H H H OH 1 D109 CH₃ H H H OH 1 D110 CH₃OC(O) CH₃ H H OH 1 D111 CH₃CH₂OC(O) CH₃ H H OH 1 D112 CH₃O CH₃ H H OH 1 D113 CH₃S CH₃ H H OH 1 D114 CH₃SO CH₃ H H OH 1 D115 CH₃SO₂ CH₃ H H OH 1 D116 CH₃CH₂ H H H OH 1 D117 CH₃OC(O) CH₃CH₂ H H OH 1 D118 CH₃CH₂OC(O) CH₃CH₂ H H OH 1 D119 CH₃O CH₃CH₂ H H OH 1 D120 CH₃S CH₃CH₂ H H OH 1 D121 CH₃SO CH₃CH₂ H H OH 1 D122 CH₃SO₂ CH₃CH₂ H H OH 1 D123 CH₃CH₂S CH₃ H H OH 1 D124 CH₃CH₂SO CH₃ H H OH 1 D125 CH₃CH₂SO₂ CH₃ H H OH 1 D126 CH₃CH₂S CH₃CH₂ H H OH 1 D127 CH₃CH₂SO CH₃CH₂ H H OH 1 D128 CH₃CH₂SO₂ CH₃CH₂ H H OH 1 D129 H H CH₃ H OH 1 D130 CH₃ H CH₃ H OH 1 D131 CH₃OC(O) CH₃ CH₃ H OH 1 D132 CH₃CH₂OC(O) CH₃ CH₃ H OH 1 D133 CH₃O CH₃ CH₃ H OH 1 D134 CH₃S CH₃ CH₃ H OH 1 0135 CH₃SO CH₃ CH₃ H OH 1 D136 CH₃SO₂ CH₃ CH₃ H OH 1 D137 H H H CH₃ OH 1 D138 CH₃ H H CH₃ OH 1 D139 H H CH₃ CH₃ OH 1 D140 CH₃CH₂OC(O) CH₃ H H OH 4

In Table 5 which follows, 0 is Q₄

and Q₄ the following radicals E:

TABLE 5 Radicals E: Radical R₆ R₇ R₁₀ X Y W q E1 H H OH S CH₂ CH₂ 2 E2 CH₃ H OH S CH₂ CH₂ 2 E3 CH₃ CH₃ OH S CH₂ CH₂ 2 E4 CH₃OC(O) H OH S CH₂ CH₂ 2 E5 CH₃ CH₃OC(O) OH S CH₂ CH₂ 2 E6 H H OH SO CH₂ CH₂ 2 E7 CH₃ H OH SO CH₂ CH₂ 2 E8 CH₃ CH₃ OH SO CH₂ CH₂ 2 E9 CH₃OC(O) H OH SO CH₂ CH₂ 2 E10 CH₃ CH₃OC(O) OH SO CH₂ CH₂ 2 E11 H H OH SO₂ CH₂ CH₂ 2 E12 CH₃ H OH SO₂ CH₂ CH₂ 2 E13 CH₃ CH₃ OH SO₂ CH₂ CH₂ 2 E14 CH₃OC(O) H OH SO₂ CH₂ CH₂ 2 E15 CH₃ CH₃OC(O) OH SO₂ CH₂ CH₂ 2 E16 H H OH CO O CH₂ 2 E17 CH₃ H OH CO O CH₂ 2 E18 CH₃ CH₃ OH CO O CH₂ 2 E19 CH₃OC(O) H OH CO O CH₂ 2 E20 CH₃ CH₃OC(O) OH CO O CH₂ 2 E21 H H OH CO O CH₂ 2 E22 CH₃ H OH CO O CH₂ 2 E23 CH₃ CH₃ OH CO O CH₂ 2 E24 CH₃OC(O) H OH CO O CH₂ 2 E25 CH₃ CH₃OC(O) OH CO O CH₂ 2 E26 H H OH CO O CH₂ 2 E27 CH₃ H OH CO O CH₂ 2 E28 CH₃ CH₃ OH CO O CH₂ 2 E29 CH₃OC(O) H OH CO O CH₂ 2 E30 CH₃ CH₃OC(O) OH CO O CH₂ 2

In Table 6 which follows, Q is Q₅

and Q₅ the radicals F which follow:

TABLE 6 Radicals F: Radical R₆ R₇ R₈ R₁₀ F1 H H H OH F2 CH₃ H H OH F3 CH₃ CH₃ H OH F4 CH₃ CH₃ CH₃ OH F5 H H CH₃ OH F6 H CH₃ CH₃ OH

TABLE 7 Compounds of the formula Ia (Ia)

Comp. No. R₂ R₃ R₄ R₅ Q₁ p A1 H H H CF₃ B24 0 A2 CH₃ H H CF₃ B24 0 A3 CH₃CH₂ H H CF₃ B24 0 A4 (CH₃)₂CH H H CF₃ B24 0 A5 (CH₃)₃C H H CF₃ B24 0 A6 cyclopropyl H H CF₃ B24 0 A7 CH₃(CH₂)₂ H H CF₃ B24 0 A8 CH₃OCH₂ H H CF₃ B24 0 A9 CH₃O(CH₂)₂ H H CF₃ B24 0 A10 Ph H H CF₃ B24 0 A11 PhO H H CF₃ B24 0 A12 PhS H H CF₃ B24 0 A13 PhSO H H CF₃ B24 0 A14 PhSO₂ H H CF₃ B24 0 A15 CH₃S H H CF₃ B24 0 A16 CH₃SO H H CF₃ B24 0 A17 CF₃ H H CF₃ B24 0 A18 F₂CH H H CF₃ B24 0 A19 HCC H H CF₃ B24 0 A20 CH₃CC H H CF₃ B24 0 A21 CH₂═CH H H CF₃ B24 0 A22 CH₂═CHCH₂ H H CF₃ B24 0 A23 CH₃SO₂N(CH₃) H H CF₃ B24 0 A24 (CH₃)₂N H H CF₃ B24 0 A25 (CH₃)₂NSO₂ H H CF₃ B24 0 A26 ClCH₂ H H CF₃ B24 0 A27 CH₃SCH₂ H H CF₃ B24 0 A28 CH₃SOCH₂ H H CF₃ B24 0 A29 CH₃SO₂CH₂ H H CF₃ B24 0 A30 [1.2.4]-triazol-1- H H CF₃ B24 0 ylmethyl A31 CH₃ CF₃ H CH₃ B24 0 A32 CH₃ CH₃ H CF₃ B24 0 A33 H H H CF₃CF₂ B24 0 A34 CH₃ H H CF₃CF₂ B24 0 A35 CH₃CH₂ H H CF₃CF₂ B24 0 A36 cyclopropyl H H CF₃CF₂ B24 0 A37 (CH₃)₃C H H CF₃CF₂ B24 0 A38 (CH₃)₂CH H H CF₃CF₂ B24 0 A39 CH₃(CH₂)₂ H H CF₃CF₂ B24 0 A40 CH₃OCH₂ H H CF₃CF₂ B24 0 A41 CH₃O(CH₂)₂ H H CF₃CF₂ B24 0 A42 Ph H H CF₃CF₂ B24 0 A43 PhO H H CF₃CF₂ B24 0 A44 PhS H H CF₃CF₂ B24 0 A45 PhSO H H CF₃CF₂ B24 0 A46 PhSO₂ H H CF₃CF₂ B24 0 A47 CH₃S H H CF₃CF₂ B24 0 A48 CH₃SO H H CF₃CF₂ B24 0 A49 CF₃ H H CF₃CF₂ B24 0 A50 F₂CH H H CF₃CF₂ B24 0 A51 HCC H H CF₃CF₂ B24 0 A52 CH₃CC H H CF₃CF₂ B24 0 A53 CH₂═CH H H CF₃CF₂ B24 0 A54 CH₂═CHCH₂ H H CF₃CF₂ B24 0 A55 CH₃SO₂N(CH₃) H H CF₃CF₂ B24 0 A56 (CH₃)₂N H H CF₃CF₂ B24 0 A57 (CH₃)₂NSO₂ H H CF₃CF₂ B24 0 A58 ClCH₂ H H CF₃CF₂ B24 0 A59 CH₃SCH₂ H H CF₃CF₂ B24 0 A60 CH₃SOCH₂ H H CF₃CF₂ B24 0 A61 CH₃SO₂CH₂ H H CF₃CF₂ B24 0 A62 [1.2.4]-triazol-1- H H CF₃CF₂ B24 0 ylmethyl A63 H H H CF₃CF₂CF₂ B24 0 A64 CH₃ H H CF₃CF₂CF₂ B24 0 A65 CH₃CH₂ H H CF₃CF₂CF₂ B24 0 A66 cyclopropyl H H CF₃CF₂CF₂ B24 0 A67 (CH₃)₃C H H CF₃CF₂CF₂ B24 0 A68 (CH₃)₂CH H H CF₃CF₂CF₂ B24 0 A69 CH₃(CH₂)₂ H H CF₃CF₂CF₂ B24 0 A70 CH₃OCH₂ H H CF₃CF₂CF₂ B24 0 A71 CH₃O(CH₂)₂ H H CF₃CF₂CF₂ B24 0 A72 Ph H H CF₃CF₂CF₂ B24 0 A73 PhO H H CF₃CF₂CF₂ B24 0 A74 PhS H H CF₃CF₂CF₂ B24 0 A75 PhSO H H CF₃CF₂CF₂ B24 0 A76 PhSO₂ H H CF₃CF₂CF₂ B24 0 A77 CH₃S H H CF₃CF₂CF₂ B24 0 A78 CH₃SO H H CF₃CF₂CF₂ B24 0 A79 CF₃ H H CF₃CF₂CF₂ B24 0 A80 F₂CH H H CF₃CF₂CF₂ B24 0 A81 HCC H H CF₃CF₂CF₂ B24 0 A82 CH₃CC H H CF₃CF₂CF₂ B24 0 A83 CH₂═CH H H CF₃CF₂CF₂ B24 0 A84 CH₂═CHCH₂ H H CF₃CF₂CF₂ B24 0 A85 CH₃SO₂N(CH₃) H H CF₃CF₂CF₂ B24 0 A86 (CH₃)₂N H H CF₃CF₂CF₂ B24 0 A87 (CH₃)₂NSO₂ H H CF₃CF₂CF₂ B24 0 A88 ClCH₂ H H CF₃CF₂CF₂ B24 0 A89 CH₃SCH₂ H H CF₃CF₂CF₂ B24 0 A90 CH₃SOCH₂ H H CF₃CF₂CF₂ B24 0 A91 CH₃SO₂CH₂ H H CF₃CF₂CF₂ B24 0 A92 [1.2.4]-triazol-1- H H CF₃CF₂CF₂ B24 0 ylmethyl A93 H H H CF₂Cl B24 0 A94 CH₃ H H CF₂Cl B24 0 A95 CH₃CH₂ H H CF₂Cl B24 0 A96 cyclopropyl H H CF₂Cl B24 0 A97 (CH₃)₃C H H CF₂Cl B24 0 A98 (CH₃)₂CH H H CF₂Cl B24 0 A99 CH₃(CH₂)₂ H H CF₂Cl B24 0 A100 CH₃OCH₂ H H CF₂Cl B24 0 A101 CH₃O(CH₂)₂ H H CF₂Cl B24 0 A102 Ph H H CF₂Cl B24 0 A103 PhO H H CF₂Cl B24 0 A104 PhS H H CF₂Cl B24 0 A105 PhSO H H CF₂Cl B24 0 A106 PhSO₂ H H CF₂Cl B24 0 A107 CH₃S H H CF₂Cl B24 0 A108 CH₃SO H H CF₂Cl B24 0 A109 CF₃ H H CF₂Cl B24 0 A110 F₂CH H H CF₂Cl B24 0 A111 HCC H H CF₂Cl B24 0 A112 CH₃CC H H CF₂Cl B24 0 A113 CH₂═CH H H CF₂Cl B24 0 A114 CH₂═CHCH₂ H H CF₂Cl B24 0 A115 CH₃SO₂N(CH₃) H H CF₂Cl B24 0 A116 (CH₃)₂N H H CF₂Cl B24 0 A117 (CH₃)₂NSO₂ H H CF₂Cl B24 0 A118 ClCH₂ H H CF₂Cl B24 0 A119 CH₃SCH₂ H H CF₂Cl B24 0 A120 CH₃SOCH₂ H H CF₂Cl B24 0 A121 CH₃SO₂CH₂ H H CF₂Cl B24 0 A122 [1.2.4]-triazol-1- H H CF₂Cl B24 0 ylmethyl A123 H H H CHF₂ B24 0 A124 CH₃ H H CHF₂ B24 0 A125 CH₃CH₂ H H CHF₂ B24 0 A126 cyclopropyl H H CHF₂ B24 0 A127 (CH₃)₃C H H CHF₂ B24 0 A128 (CH₃)₂CH H H CHF₂ B24 0 A129 CH₃(CH₂)₂ H H CHF₂ B24 0 A130 CH₃OCH₂ H H CHF₂ B24 0 A131 CH₃O(CH₂)₂ H H CHF₂ B24 0 A132 Ph H H CHF₂ B24 0 A133 PhO H H CHF₂ B24 0 A134 PhS H H CHF₂ B24 0 A135 PhSO H H CHF₂ B24 0 A136 PhSO₂ H H CHF₂ B24 0 A137 CH₃S H H CHF₂ B24 0 A138 CH₃SO H H CHF₂ B24 0 A139 CF₃ H H CHF₂ B24 0 A140 F₂CH H H CHF₂ B24 0 A141 HCC H H CHF₂ B24 0 A142 CH₃CC H H CHF₂ B24 0 A143 CH₂═CH H H CHF₂ B24 0 A144 CH₂═CHCH₂ H H CHF₂ B24 0 A145 CH₃SO₂N(CH₃) H H CHF₂ B24 0 A146 (CH₃)₂N H H CHF₂ B24 0 A147 (CH₃)₂NSO₂ H H CHF₂ B24 0 A148 ClCH₂ H H CHF₂ B24 0 A149 CH₃SCH₂ H H CHF₂ B24 0 A150 CH₃SOCH₂ H H CHF₂ B24 0 A151 CH₃SO₂CH₂ H H CHF₂ B24 0 A152 [1.2.4]-triazol-1- H H CHF₂ B24 0 ylmethyl A153 H H H CCl₃ B24 0 A154 CH₃ H H CCl₃ B24 0 A155 CH₃CH₂ H H CCl₃ B24 0 A156 cyclopropyl H H CCl₃ B24 0 A157 (CH₃)₃C H H CCl₃ B24 0 A158 (CH₃)₂CH H H CCl₃ B24 0 A159 CH₃(CH₂)₂ H H CCl₃ B24 0 A160 CH₃OCH₂ H H CCl₃ B24 0 A161 CH₃O(CH₂)₂ H H CCl₃ B24 0 A162 Ph H H CCl₃ B24 0 A163 PhO H H CCl₃ B24 0 A164 PhS H H CCl₃ B24 0 A165 PhSO H H CCl₃ B24 0 A166 PhSO₂ H H CCl₃ B24 0 A167 CH₃S H H CCl₃ B24 0 A168 CH₃SO H H CCl₃ B24 0 A169 CF₃ H H CCl₃ B24 0 A170 F₂CH H H CCl₃ B24 0 A171 HCC H H CCl₃ B24 0 A172 CH₃CC H H CCl₃ B24 0 A173 CH₂═CH H H CCl₃ B24 0 A174 CH₂═CHCH₂ H H CCl₃ B24 0 A175 CH₃SO₂N(CH₃) H H CCl₃ B24 0 A176 (CH₃)₂N H H CCl₃ B24 0 A177 (CH₃)₂NSO₂ H H CCl₃ B24 0 A178 ClCH₂ H H CCl₃ B24 0 A179 CH₃SCH₂ H H CCl₃ B24 0 A180 CH₃SOCH₂ H H CCl₃ B24 0 A181 CH₃SO₂CH₂ H H CCl₃ B24 0 A182 [1.2.4]-triazol-1- H H CCl₃ B24 0 ylmethyl A183 H H CH₃ CF₃ B24 0 A184 CH₃ H CH₃ CF₃ B24 0 A185 CH₃CH₂ H CH₃ CF₃ B24 0 A186 cyclopropyl H CH₃ CF₃ B24 0 A187 (CH₃)₃C H CH₃ CF₃ B24 0 A188 (CH₃)₂CH H CH₃ CF₃ B24 0 A189 CH₃(CH₂)₂ H CH₃ CF₃ B24 0 A190 CH₃OCH₂ H CH₃ CF₃ B24 0 A191 CH₃O(CH₂)₂ H CH₃ CF₃ B24 0 A192 Ph H CH₃ CF₃ B24 0 A193 PhO H CH₃ CF₃ B24 0 A194 PhS H CH₃ CF₃ B24 0 A195 PhSO H CH₃ CF₃ B24 0 A196 PhSO₂ H CH₃ CF₃ B24 0 A197 CH₃S H CH₃ CF₃ B24 0 A198 CH₃SO H CH₃ CF₃ B24 0 A199 CF₃ H CH₃ CF₃ B24 0 A200 F₂CH H CH₃ CF₃ B24 0 A201 HCC H CH₃ CF₃ B24 0 A202 CH₃CC H CH₃ CF₃ B24 0 A203 CH₂═CH H CH₃ CF₃ B24 0 A204 CH₂═CHCH₂ H CH₃ CF₃ B24 0 A205 CH₃SO₂N(CH₃) H CH₃ CF₃ B24 0 A206 (CH₃)₂N H CH₃ CF₃ B24 0 A207 (CH₃)₂NSO₂ H CH₃ CF₃ B24 0 A208 ClCH₂ H CH₃ CF₃ B24 0 A209 CH₃SCH₂ H CH₃ CF₃ B24 0 A210 CH₃SOCH₂ H CH₃ CF₃ B24 0 A211 CH₃SO₂CH₂ H CH₃ CF₃ B24 0 A212 H H CH₃ CF₃CF₂ B24 0 A213 CH₃ H CH₃ CF₃CF₂ B24 0 A214 CH₃CH₂ H CH₃ CF₃CF₂ B24 0 A215 cyclopropyl H CH₃ CF₃CF₂ B24 0 A216 (CH₃)₃C H CH₃ CF₃CF₂ B24 0 A217 (CH₃)₂CH H CH₃ CF₃CF₂ B24 0 A218 CH₃(CH₂)₂ H CH₃ CF₃CF₂ B24 0 A219 CH₃OCH₂ H CH₃ CF₃CF₂ B24 0 A220 CH₃O(CH₂)₂ H CH₃ CF₃CF₂ B24 0 A221 Ph H CH₃ CF₃CF₂ B24 0 A222 PhO H CH₃ CF₃CF₂ B24 0 A223 PhS H CH₃ CF₃CF₂ B24 0 A224 PhSO H CH₃ CF₃CF₂ B24 0 A225 PhSO₂ H CH₃ CF₃CF₂ B24 0 A226 CH₃S H CH₃ CF₃CF₂ B24 0 A227 CH₃SO H CH₃ CF₃CF₂ B24 0 A228 CF₃ H CH₃ CF₃CF₂ B24 0 A229 F₂CH H CH₃ CF₃CF₂ B24 0 A230 HCC H CH₃ CF₃CF₂ B24 0 A231 CH₃CC H CH₃ CF₃CF₂ B24 0 A232 CH₂═CH H CH₃ CF₃CF₂ B24 0 A233 CH₂═CHCH₂ H CH₃ CF₃CF₂ B24 0 A234 CH₃SO₂N(CH₃) H CH₃ CF₃CF₂ B24 0 A235 (CH₃)₂N H CH₃ CF₃CF₂ B24 0 A236 (CH₃)₂NSO₂ H CH₃ CF₃CF₂ B24 0 A237 ClCH₂ H CH₃ CF₃CF₂ B24 0 A238 CH₃SCH₂ H CH₃ CF₃CF₂ B24 0 A239 CH₃SOCH₂ H CH₃ CF₃CF₂ B24 0 A240 CH₃SO₂CH₂ H CH₃ CF₃CF₂ B24 0 A241 H H CH₃ CF₃CF₂CF₂ B24 0 A242 CH₃ H CH₃ CF₃CF₂CF₂ B24 0 A243 CH₃CH₂ H CH₃ CF₃CF₂CF₂ B24 0 A244 cyclopropyl H CH₃ CF₃CF₂CF₂ B24 0 A245 (CH₃)₃C H CH₃ CF₃CF₂CF₂ B24 0 A246 (CH₃)₂CH H CH₃ CF₃CF₂CF₂ B24 0 A247 CH₃(CH₂)₂ H CH₃ CF₃CF₂CF₂ B24 0 A248 CH₃OCH₂ H CH₃ CF₃CF₂CF₂ B24 0 A249 CH₃O(CH₂)₂ H CH₃ CF₃CF₂CF₂ B24 0 A250 Ph H CH₃ CF₃CF₂CF₂ B24 0 A251 PhO H CH₃ CF₃CF₂CF₂ B24 0 A252 PhS H CH₃ CF₃CF₂CF₂ B24 0 A253 PhSO H CH₃ CF₃CF₂CF₂ B24 0 A254 PhSO₂ H CH₃ CF₃CF₂CF₂ B24 0 A255 CH₃S H CH₃ CF₃CF₂CF₂ B24 0 A256 CH₃SO H CH₃ CF₃CF₂CF₂ B24 0 A257 CF₃ H CH₃ CF₃CF₂CF₂ B24 0 A258 F₂CH H CH₃ CF₃CF₂CF₂ B24 0 A259 HCC H CH₃ CF₃CF₂CF₂ B24 0 A260 CH₃CC H CH₃ CF₃CF₂CF₂ B24 0 A261 CH₂═CH H CH₃ CF₃CF₂CF₂ B24 0 A262 CH₂═CHCH₂ H CH₃ CF₃CF₂CF₂ B24 0 A263 CH₃SO₂N(CH₃) H CH₃ CF₃CF₂CF₂ B24 0 A264 (CH₃)₂N H CH₃ CF₃CF₂CF₂ B24 0 A265 (CH₃)₂NSO₂ H CH₃ CF₃CF₂CF₂ B24 0 A266 ClCH₂ H CH₃ CF₃CF₂CF₂ B24 0 A267 CH₃SCH₂ H CH₃ CF₃CF₂CF₂ B24 0 A268 CH₃SOCH₂ H CH₃ CF₃CF₂CF₂ B24 0 A269 CH₃SO₂CH₂ H CH₃ CF₃CF₂CF₂ B24 0 A270 H H CH₃ CF₂Cl B24 0 A271 CH₃ H CH₃ CF₂Cl B24 0 A272 CH₃CH₂ H CH₃ CF₂Cl B24 0 A273 cyclopropyl H CH₃ CF₂Cl B24 0 A274 (CH₃)₃C H CH₃ CF₂Cl B24 0 A275 (CH₃)₂CH H CH₃ CF₂Cl B24 0 A276 CH₃(CH₂)₂ H CH₃ CF₂Cl B24 0 A277 CH₃OCH₂ H CH₃ CF₂Cl B24 0 A278 CH₃O(CH₂)₂ H CH₃ CF₂Cl B24 0 A279 Ph H CH₃ CF₂Cl B24 0 A280 PhO H CH₃ CF₂Cl B24 0 A281 PhS H CH₃ CF₂Cl B24 0 A282 PhSO H CH₃ CF₂Cl B24 0 A283 PhSO₂ H CH₃ CF₂Cl B24 0 A284 CH₃S H CH₃ CF₂Cl B24 0 A285 CH₃SO H CH₃ CF₂Cl B24 0 A286 CF₃ H CH₃ CF₂Cl B24 0 A287 F₂CH H CH₃ CF₂Cl B24 0 A288 HCC H CH₃ CF₂Cl B24 0 A289 CH₃CC H CH₃ CF₂Cl B24 0 A290 CH₂═CH H CH₃ CF₂Cl B24 0 A291 CH₂═CHCH₂ H CH₃ CF₂Cl B24 0 A292 CH₃SO₂N(CH₃) H CH₃ CF₂Cl B24 0 A293 (CH₃)₂N H CH₃ CF₂Cl B24 0 A294 (CH₃)₂NSO₂ H CH₃ CF₂Cl B24 0 A295 ClCH₂ H CH₃ CF₂Cl B24 0 A296 CH₃SCH₂ H CH₃ CF₂Cl B24 0 A297 CH₃SOCH₂ H CH₃ CF₂Cl B24 0 A298 CH₃SO₂CH₂ H CH₃ CF₂Cl B24 0 A299 H H CH₃ CHF₂ B24 0 A300 CH₃ H CH₃ CHF₂ B24 0 A301 CH₃CH₂ H CH₃ CHF₂ B24 0 A302 cyclopropyl H CH₃ CHF₂ B24 0 A303 (CH₃)₃C H CH₃ CHF₂ B24 0 A304 (CH₃)₂CH H CH₃ CHF₂ B24 0 A305 CH₃(CH₂)₂ H CH₃ CHF₂ B24 0 A306 CH₃OCH₂ H CH₃ CHF₂ B24 0 A307 CH₃O(CH₂)₂ H CH₃ CHF₂ B24 0 A308 Ph H CH₃ CHF₂ B24 0 A309 PhO H CH₃ CHF₂ B24 0 A310 PhS H CH₃ CHF₂ B24 0 A311 PhSO H CH₃ CHF₂ B24 0 A312 PhSO₂ H CH₃ CHF₂ B24 0 A313 CH₃S H CH₃ CHF₂ B24 0 A314 CH₃SO H CH₃ CHF₂ B24 0 A315 CF₃ H CH₃ CHF₂ B24 0 A316 F₂CH H CH₃ CHF₂ B24 0 A317 HCC H CH₃ CHF₂ B24 0 A318 CH₃CC H CH₃ CHF₂ B24 0 A319 CH₂═CH H CH₃ CHF₂ B24 0 A320 CH₂═CHCH₂ H CH₃ CHF₂ B24 0 A321 CH₃SO₂N(CH₃) H CH₃ CHF₂ B24 0 A322 (CH₃)₂N H CH₃ CHF₂ B24 0 A323 (CH₃)₂NSO₂ H CH₃ CHF₂ B24 0 A324 ClCH₂ H CH₃ CHF₂ B24 0 A325 CH₃SCH₂ H CH₃ CHF₂ B24 0 A326 CH₃SOCH₂ H CH₃ CHF₂ B24 0 A327 CH₃SO₂CH₂ H CH₃ CHF₂ B24 0 A328 H H CH₃ CCl₃ B24 0 A329 CH₃ H CH₃ CCl₃ B24 0 A330 CH₃CH₂ H CH₃ CCl₃ B24 0 A331 (CH₃)₃C H CH₃ CCl₃ B24 0 A332 (CH₃)₂CH H CH₃ CCl₃ B24 0 A333 cyclopropyl H CH₃ CCl₃ B24 0 A334 CH₃(CH₂)₂ H CH₃ CCl₃ B24 0 A335 CH₃OCH₂ H CH₃ CCl₃ B24 0 A336 CH₃O(CH₂)₂ H CH₃ CCl₃ B24 0 A337 Ph H CH₃ CCl₃ B24 0 A338 PhO H CH₃ CCl₃ B24 0 A339 PhS H CH₃ CCl₃ B24 0 A340 PhSO H CH₃ CCl₃ B24 0 A341 PhSO₂ H CH₃ CCl₃ B24 0 A342 CH₃S H CH₃ CCl₃ B24 0 A343 CH₃SO H CH₃ CCl₃ B24 0 A344 CF₃ H CH₃ CCl₃ B24 0 A345 F₂CH H CH₃ CCl₃ B24 0 A346 HCC H CH₃ CCl₃ B24 0 A347 CH₃CC H CH₃ CCl₃ B24 0 A348 CH₂═CH H CH₃ CCl₃ B24 0 A349 CH₂═CHCH₂ H CH₃ CCl₃ B24 0 A350 CH₃SO₂N(CH₃) H CH₃ CCl₃ B24 0 A351 (CH₃)₂N H CH₃ CCl₃ B24 0 A352 (CH₃)₂NSO₂ H CH₃ CCl₃ B24 0 A353 ClCH₂ H CH₃ CCl₃ B24 0 A354 CH₃SCH₂ H CH₃ CCl₃ B24 0 A355 CH₃SOCH₂ H CH₃ CCl₃ B24 0 A356 CH₃SO₂CH₂ H CH₃ CCl₃ B24 0 A357 H H Ph CF₃ B24 0 A358 CH₃ H Ph CF₃ B24 0 A359 CH₃CH₂ H Ph CF₃ B24 0 A360 cyclopropyl H Ph CF₃ B24 0 A361 (CH₃)₃C H Ph CF₃ B24 0 A362 (CH₃)₂CH H Ph CF₃ B24 0 A363 CH₃(CH₂)₂ H Ph CF₃ B24 0 A364 CH₃OCH₂ H Ph CF₃ B24 0 A365 CH₃O(CH₂)₂ H Ph CF₃ B24 0 A366 Ph H Ph CF₃ B24 0 A367 PhO H Ph CF₃ B24 0 A368 PhS H Ph CF₃ B24 0 A369 PhSO H Ph CF₃ B24 0 A370 PhSO₂ H Ph CF₃ B24 0 A371 CH₃S H Ph CF₃ B24 0 A372 CH₃SO H Ph CF₃ B24 0 A373 CF₃ H Ph CF₃ B24 0 A374 F₂CH H Ph CF₃ B24 0 A375 HCC H Ph CF₃ B24 0 A376 CH₃CC H Ph CF₃ B24 0 A377 CH₂═CH H Ph CF₃ B24 0 A378 CH₂═CHCH₂ H Ph CF₃ B24 0 A379 CH₃SO₂N(CH₃) H Ph CF₃ B24 0 A380 (CH₃)₂N H Ph CF₃ B24 0 A381 (CH₃)₂NSO₂ H Ph CF₃ B24 0 A382 ClCH₂ H Ph CF₃ B24 0 A383 CH₃SCH₂ H Ph CF₃ B24 0 A384 CH₃SOCH₂ H Ph CF₃ B24 0 A385 CH₃SO₂CH₂ H Ph CF₃ B24 0 A386 H H Ph CF₃CF₂ B24 0 A387 CH₃ H Ph CF₃CF₂ B24 0 A388 CH₃CH₂ H Ph CF₃CF₂ B24 0 A389 cyclopropyl H Ph CF₃CF₂ B24 0 A390 (CH₃)₃C H Ph CF₃CF₂ B24 0 A391 (CH₃)₂CH H Ph CF₃CF₂ B24 0 A392 CH₃(CH₂)₂ H Ph CF₃CF₂ B24 0 A393 CH₃OCH₂ H Ph CF₃CF₂ B24 0 A394 CH₃O(CH₂)₂ H Ph CF₃CF₂ B24 0 A395 Ph H Ph CF₃CF₂ B24 0 A396 PhO H Ph CF₃CF₂ B24 0 A397 PhS H Ph CF₃CF₂ B24 0 A398 PhSO H Ph CF₃CF₂ B24 0 A399 PhSO₂ H Ph CF₃CF₂ B24 0 A400 CH₃S H Ph CF₃CF₂ B24 0 A401 CH₃SO H Ph CF₃CF₂ B24 0 A402 CF₃ H Ph CF₃CF₂ B24 0 A403 F₂CH H Ph CF₃CF₂ B24 0 A404 HCC H Ph CF₃CF₂ B24 0 A405 CH₃CC H Ph CF₃CF₂ B24 0 A406 CH₂═CH H Ph CF₃CF₂ B24 0 A407 CH₂═CHCH₂ H Ph CF₃CF₂ B24 0 A408 CH₃SO₂N(CH₃) H Ph CF₃CF₂ B24 0 A409 (CH₃)₂N H Ph CF₃CF₂ B24 0 A410 (CH₃)₂NSO₂ H Ph CF₃CF₂ B24 0 A411 ClCH₂ H Ph CF₃CF₂ B24 0 A412 CH₃SCH₂ H Ph CF₃CF₂ B24 0 A413 CH₃SOCH₂ H Ph CF₃CF₂ B24 0 A414 CH₃SO₂CH₂ H Ph CF₃CF₂ B24 0 A415 H H Ph CF₃CF₂CF₂ B24 0 A416 CH₃ H Ph CF₃CF₂CF₂ B24 0 A417 CH₃CH₂ H Ph CF₃CF₂CF₂ B24 0 A418 cyclopropyl H Ph CF₃CF₂CF₂ B24 0 A419 (CH₃)₃C H Ph CF₃CF₂CF₂ B24 0 A420 (CH₃)₂CH H Ph CF₃CF₂CF₂ B24 0 A421 CH₃(CH₂)₂ H Ph CF₃CF₂CF₂ B24 0 A422 CH₃OCH₂ H Ph CF₃CF₂CF₂ B24 0 A423 CH₃O(CH₂)₂ H Ph CF₃CF₂CF₂ B24 0 A424 Ph H Ph CF₃CF₂CF₂ B24 0 A425 PhO H Ph CF₃CF₂CF₂ B24 0 A426 PhS H Ph CF₃CF₂CF₂ B24 0 A427 PhSO H Ph CF₃CF₂CF₂ B24 0 A428 PhSO₂ H Ph CF₃CF₂CF₂ B24 0 A429 CH₃S H Ph CF₃CF₂CF₂ B24 0 A430 CH₃SO H Ph CF₃CF₂CF₂ B24 0 A431 CF₃ H Ph CF₃CF₂CF₂ B24 0 A432 F₂CH H Ph CF₃CF₂CF₂ B24 0 A433 HCC H Ph CF₃CF₂CF₂ B24 0 A434 CH₃CC H Ph CF₃CF₂CF₂ B24 0 A435 CH₂═CH H Ph CF₃CF₂CF₂ B24 0 A436 CH₂═CHCH₂ H Ph CF₃CF₂CF₂ B24 0 A437 CH₃SO₂N(CH₃) H Ph CF₃CF₂CF₂ B24 0 A438 (CH₃)₂N H Ph CF₃CF₂CF₂ B24 0 A439 (CH₃)₂NSO₂ H Ph CF₃CF₂CF₂ B24 0 A440 ClCH₂ H Ph CF₃CF₂CF₂ B24 0 A441 CH₃SCH₂ H Ph CF₃CF₂CF₂ B24 0 A442 CH₃SOCH₂ H Ph CF₃CF₂CF₂ B24 0 A443 CH₃SO₂CH₂ H Ph CF₃CF₂CF₂ B24 0 A444 H H Ph CF₂Cl B24 0 A445 CH₃ H Ph CF₂Cl B24 0 A446 CH₃CH₂ H Ph CF₂Cl B24 0 A447 cyclopropyl H Ph CF₂Cl B24 0 A448 (CH₃)₃C H Ph CF₂Cl B24 0 A449 (CH₃)₂CH H Ph CF₂Cl B24 0 A450 CH₃(CH₂)₂ H Ph CF₂Cl B24 0 A451 CH₃OCH₂ H Ph CF₂Cl B24 0 A452 CH₃O(CH₂)₂ H Ph CF₂Cl B24 0 A453 Ph H Ph CF₂Cl B24 0 A454 PhO H Ph CF₂Cl B24 0 A455 PhS H Ph CF₂Cl B24 0 A456 PhSO H Ph CF₂Cl B24 0 A457 PhSO₂ H Ph CF₂Cl B24 0 A458 CH₃S H Ph CF₂Cl B24 0 A459 CH₃SO H Ph CF₂Cl B24 0 A460 CF₃ H Ph CF₂Cl B24 0 A461 F₂CH H Ph CF₂Cl B24 0 A462 HCC H Ph CF₂Cl B24 0 A463 CH₃CC H Ph CF₂Cl B24 0 A464 CH₂═CH H Ph CF₂Cl B24 0 A465 CH₂═CHCH₂ H Ph CF₂Cl B24 0 A466 CH₃SO₂N(CH₃) H Ph CF₂Cl B24 0 A467 (CH₃)₂N H Ph CF₂Cl B24 0 A468 (CH₃)₂NSO₂ H Ph CF₂Cl B24 0 A469 ClCH₂ H Ph CF₂Cl B24 0 A470 CH₃SCH₂ H Ph CF₂Cl B24 0 A471 CH₃SOCH₂ H Ph CF₂Cl B24 0 A472 CH₃SO₂CH₂ H Ph CF₂Cl B24 0 A473 H H Ph CHF₂ B24 0 A474 CH₃ H Ph CHF₂ B24 0 A475 CH₃CH₂ H Ph CHF₂ B24 0 A476 cyclopropyl H Ph CHF₂ B24 0 A477 (CH₃)₃C H Ph CHF₂ B24 0 A478 (CH₃)₂CH H Ph CHF₂ B24 0 A479 CH₃(CH₂)₂ H Ph CHF₂ B24 0 A480 CH₃OCH₂ H Ph CHF₂ B24 0 A481 CH₃O(CH₂)₂ H Ph CHF₂ B24 0 A482 Ph H Ph CHF₂ B24 0 A483 PhO H Ph CHF₂ B24 0 A484 PhS H Ph CHF₂ B24 0 A485 PhSO H Ph CHF₂ B24 0 A486 PhSO₂ H Ph CHF₂ B24 0 A487 CH₃S H Ph CHF₂ B24 0 A488 CH₃SO H Ph CHF₂ B24 0 A489 CF₃ H Ph CHF₂ B24 0 A490 F₂CH H Ph CHF₂ B24 0 A491 HCC H Ph CHF₂ B24 0 A492 CH₃CC H Ph CHF₂ B24 0 A493 CH₂═CH H Ph CHF₂ B24 0 A494 CH₂═CHCH₂ H Ph CHF₂ B24 0 A495 CH₃SO₂N(CH₃) H Ph CHF₂ B24 0 A496 (CH₃)₂N H Ph CHF₂ B24 0 A497 (CH₃)₂NSO₂ H Ph CHF₂ B24 0 A498 ClCH₂ H Ph CHF₂ B24 0 A499 CH₃SCH₂ H Ph CHF₂ B24 0 A500 CH₃SOCH₂ H Ph CHF₂ B24 0 A501 CH₃SO₂CH₂ H Ph CHF₂ B24 0 A502 H H Ph CCl₃ B24 0 A503 CH₃ H Ph CCl₃ B24 0 A504 CH₃CH₂ H Ph CCl₃ B24 0 A505 cyclopropyl H Ph CCl₃ B24 0 A506 (CH₃)₃C H Ph CCl₃ B24 0 A507 (CH₃)₂CH H Ph CCl₃ B24 0 A508 CH₃(CH₂)₂ H Ph CCl₃ B24 0 A509 CH₃OCH₂ H Ph CCl₃ B24 0 A510 CH₃O(CH₂)₂ H Ph CCl₃ B24 0 A511 Ph H Ph CCl₃ B24 0 A512 PhO H Ph CCl₃ B24 0 A513 PhS H Ph CCl₃ B24 0 A514 PhSO H Ph CCl₃ B24 0 A515 PhSO₂ H Ph CCl₃ B24 0 A516 CH₃S H Ph CCl₃ B24 0 A517 CH₃SO H Ph CCl₃ B24 0 A518 CF₃ H Ph CCl₃ B24 0 A519 F₂CH H Ph CCl₃ B24 0 A520 HCC H Ph CCl₃ B24 0 A521 CH₃CC H Ph CCl₃ B24 0 A522 CH₂═CH H Ph CCl₃ B24 0 A523 CH₂═CHCH₂ H Ph CCl₃ B24 0 A524 CH₃SO₂N(CH₃) H Ph CCl₃ B24 0 A525 (CH₃)₂N H Ph CCl₃ B24 0 A526 (CH₃)₂NSO₂ H Ph CCl₃ B24 0 A527 ClCH₂ H Ph CCl₃ B24 0 A528 CH₃SCH₂ H Ph CCl₃ B24 0 A529 CH₃SOCH₂ H Ph CCl₃ B24 0 A530 CH₃SO₂CH₂ H Ph CCl₃ B24 0 A531 H CH₃ H CF₃ B24 0 A532 H CH₃CH₂ H CF₃ B24 0 A533 H cyclopropyl H CF₃ B24 0 A534 H (CH₃)₃CH H CF₃ B24 0 A535 H (CH₃)₂CH H CF₃ B24 0 A536 H CH₃(CH₂)₂ H CF₃ B24 0 A537 H CH₃OCH₂ H CF₃ B24 0 A538 H CH₃O(CH₂)₂ H CF₃ B24 0 A539 H Ph H CF₃ B24 0 A540 H PhO H CF₃ B24 0 A541 H PhS H CF₃ B24 0 A542 H PhSO H CF₃ B24 0 A543 H PhSO₂ H CF₃ B24 0 A544 H CH₃S H CF₃ B24 0 A545 H CH₃SO H CF₃ B24 0 A546 H CF₃ H CF₃ B24 0 A547 H F₂CH H CF₃ B24 0 A548 H HCC H CF₃ B24 0 A549 H CH₃CC H CF₃ B24 0 A550 H CH₂═CH H CF₃ B24 0 A551 H CH₂═CHCH₂ H CF₃ B24 0 A552 H CH₃SO₂N(CH₃) H CF₃ B24 0 A553 H (CH₃)₂N H CF₃ B24 0 A554 H (CH₃)₂NSO₂ H CF₃ B24 0 A555 H CH₃SCH₂ H CF₃ B24 0 A556 H CH₃SOCH₂ H CF₃ B24 0 A557 H CH₃SO₂CH₂ H CF₃ B24 0 A558 H CH₃ H CF₃CF₂ B24 0 A559 H CH₃CH₂ H CF₃CF₂ B24 0 A560 H cyclopropyl H CF₃CF₂ B24 0 A561 H (CH₃)₃C H CF₃CF₂ B24 0 A562 H (CH₃)₂CH H CF₃CF₂ B24 0 A563 H CH₃(CH₂)₂ H CF₃CF₂ B24 0 A564 H CH₃OCH₂ H CF₃CF₂ B24 0 A565 H CH₃O(CH₂)₂ H CF₃CF₂ B24 0 A566 H Ph H CF₃CF₂ B24 0 A567 H PhO H CF₃CF₂ B24 0 A568 H PhS H CF₃CF₂ B24 0 A569 H PhSO H CF₃CF₂ B24 0 A570 H PhSO₂ H CF₃CF₂ B24 0 A571 H CH₃S H CF₃CF₂ B24 0 A572 H CH₃SO H CF₃CF₂ B24 0 A573 H CF₃ H CF₃CF₂ B24 0 A574 H F₂CH H CF₃CF₂ B24 0 A575 H HCC H CF₃CF₂ B24 0 A576 H CH₃CC H CF₃CF₂ B24 0 A577 H CH₂═CH H CF₃CF₂ B24 0 A578 H CH₂═CHCH₂ H CF₃CF₂ B24 0 A579 H CH₃SO₂N(CH₃) H CF₃CF₂ B24 0 A580 H (CH₃)₂N H CF₃CF₂ B24 0 A581 H (CH₃)₂NSO₂ H CF₃CF₂ B24 0 A582 H CH₃SCH₂ H CF₃CF₂ B24 0 A583 H CH₃SOCH₂ H CF₃CF₂ B24 0 A584 H CH₃SO₂CH₂ H CF₃CF₂ B24 0 A585 H CH₃ H CF₃CF₂CF₂ B24 0 A586 H CH₃CH₂ H CF₃CF₂CF₂ B24 0 A587 H cyclopropyl H CF₃CF₂CF₂ B24 0 A588 H (CH₃)₃C H CF₃CF₂CF₂ B24 0 A589 H (CH₃)₂CH H CF₃CF₂CF₂ B24 0 A590 H CH₃(CH₂)₂ H CF₃CF₂CF₂ B24 0 A591 H CH₃OCH₂ H CF₃CF₂CF₂ B24 0 A592 H CH₃O(CH₂)₂ H CF₃CF₂CF₂ B24 0 A593 H Ph H CF₃CF₂CF₂ B24 0 A594 H PhO H CF₃CF₂CF₂ B24 0 A595 H PhS H CF₃CF₂CF₂ B24 0 A596 H PhSO H CF₃CF₂CF₂ B24 0 A597 H PhSO₂ H CF₃CF₂CF₂ B24 0 A598 H CH₃S H CF₃CF₂CF₂ B24 0 A599 H CH₃SO H CF₃CF₂CF₂ B24 0 A600 H CF₃ H CF₃CF₂CF₂ B24 0 A601 H F₂CH H CF₃CF₂CF₂ B24 0 A602 H HCC H CF₃CF₂CF₂ B24 0 A603 H CH₃CC H CF₃CF₂CF₂ B24 0 A604 H CH₂═CH H CF₃CF₂CF₂ B24 0 A605 H CH₂═CHCH₂ H CF₃CF₂CF₂ B24 0 A606 H CH₃SO₂N(CH₃) H CF₃CF₂CF₂ B24 0 A607 H (CH₃)₂N H CF₃CF₂CF₂ B24 0 A608 H (CH₃)₂NSO₂ H CF₃CF₂CF₂ B24 0 A609 H CH₃SCH₂ H CF₃CF₂CF₂ B24 0 A610 H CH₃SOCH₂ H CF₃CF₂CF₂ B24 0 A611 H CH₃SO₂CH₂ H CF₃CF₂CF₂ B24 0 A612 H CH₃ H CF₂Cl B24 0 A613 H CH₃CH₂ H CF₂Cl B24 0 A614 H cyclopropyl H CF₂Cl B24 0 A615 H (CH₃)₃C H CF₂Cl B24 0 A616 H (CH₃)₂CH H CF₂Cl B24 0 A617 H CH₃(CH₂)₂ H CF₂Cl B24 0 A618 H CH₃OCH₂ H CF₂Cl B24 0 A619 H CH₃O(CH₂)₂ H CF₂Cl B24 0 A620 H Ph H CF₂Cl B24 0 A621 H PhO H CF₂Cl B24 0 A622 H PhS H CF₂Cl B24 0 A623 H PhSO H CF₂Cl B24 0 A624 H PhSO₂ H CF₂Cl B24 0 A625 H CH₃S H CF₂Cl B24 0 A626 H CH₃SO H CF₂Cl B24 0 A627 H CF₃ H CF₂Cl B24 0 A628 H F₂CH H CF₂Cl B24 0 A629 H HCC H CF₂Cl B24 0 A630 H CH₃CC H CF₂Cl B24 0 A631 H CH₂═CH H CF₂Cl B24 0 A632 H CH₂═CHCH₂ H CF₂Cl B24 0 A633 H CH₃SO₂N(CH₃) H CF₂Cl B24 0 A634 H (CH₃)₂N H CF₂Cl B24 0 A635 H (CH₃)₂NSO₂ H CF₂Cl B24 0 A636 H CH₃SCH₂ H CF₂Cl B24 0 A637 H CH₃SOCH₂ H CF₂Cl B24 0 A638 H CH₃SO₂CH₂ H CF₂Cl B24 0 A639 H CH₃ H CHF₂ B24 0 A640 H CH₃CH₂ H CHF₂ B24 0 A641 H cyclopropyl H CHF₂ B24 0 A642 H (CH₃)₃C H CHF₂ B24 0 A643 H (CH₃)₂CH H CHF₂ B24 0 A644 H CH₃(CH₂)₂ H CHF₂ B24 0 A645 H CH₃OCH₂ H CHF₂ B24 0 A646 H CH₃O(CH₂)₂ H CHF₂ B24 0 A647 H Ph H CHF₂ B24 0 A648 H PhO H CHF₂ B24 0 A649 H PhS H CHF₂ B24 0 A650 H PhSO H CHF₂ B24 0 A651 H PhSO₂ H CHF₂ B24 0 A652 H CH₃S H CHF₂ B24 0 A653 H CH₃SO H CHF₂ B24 0 A654 H CF₃ H CHF₂ B24 0 A655 H F₂CH H CHF₂ B24 0 A656 H HCC H CHF₂ B24 0 A657 H CH₃CC H CHF₂ B24 0 A658 H CH₂═CH H CHF₂ B24 0 A659 H CH₂═CHCH₂ H CHF₂ B24 0 A660 H CH₃SO₂N(CH₃) H CHF₂ B24 0 A661 H (CH₃)₂N H CHF₂ B24 0 A662 H (CH₃)₂NSO₂ H CHF₂ B24 0 A663 H CH₃SCH₂ H CHF₂ B24 0 A664 H CH₃SOCH₂ H CHF₂ B24 0 A665 H CH₃SO₂CH₂ H CHF₂ B24 0 A666 H CH₃ H CCl₃ B24 0 A667 H CH₃CH₂ H CCl₃ B24 0 A668 H cyclopropyl H CCl₃ B24 0 A669 H (CH₃)₃C H CCl₃ B24 0 A670 H (CH₃)₂CH H CCl₃ B24 0 A671 H CH₃(CH₂)₂ H CCl₃ B24 0 A672 H CH₃OCH₂ H CCl₃ B24 0 A673 H CH₃O(CH₂)₂ H CCl₃ B24 0 A674 H Ph H CCl₃ B24 0 A675 H PhO H CCl₃ B24 0 A676 H PhS H CCl₃ B24 0 A677 H PhSO H CCl₃ B24 0 A678 H PhSO₂ H CCl₃ B24 0 A679 H CH₃S H CCl₃ B24 0 A680 H CH₃SO H CCl₃ B24 0 A681 H CF₃ H CCl₃ B24 0 A682 H F₂CH H CCl₃ B24 0 A683 H HCC H CCl₃ B24 0 A684 H CH₃CC H CCl₃ B24 0 A685 H CH₂═CH H CCl₃ B24 0 A686 H CH₂═CHCH₂ H CCl₃ B24 0 A687 H CH₃SO₂N(CH₃) H CCl₃ B24 0 A688 H (CH₃)₂N H CCl₃ B24 0 A689 H (CH₃)₂NSO₂ H CCl₃ B24 0 A690 H CH₃SCH₂ H CCl₃ B24 0 A691 H CH₃SOCH₂ H CCl₃ B24 0 A692 H CH₃SO₂CH₂ H CCl₃ B24 0 A693 H CH₃ CH₃ CF₃ B24 0 A694 H CH₃CH₂ CH₃ CF₃ B24 0 A695 H cyclopropyl CH₃ CF₃ B24 0 A696 H (CH₃)₃C CH₃ CF₃ B24 0 A697 H (CH₃)₂CH CH₃ CF₃ B24 0 A698 H CH₃(CH₂)₂ CH₃ CF₃ B24 0 A699 H CH₃OCH₂ CH₃ CF₃ B24 0 A700 H CH₃O(CH₂)₂ CH₃ CF₃ B24 0 A701 H Ph CH₃ CF₃ B24 0 A702 H PhO CH₃ CF₃ B24 0 A703 H PhS CH₃ CF₃ B24 0 A704 H PhSO CH₃ CF₃ B24 0 A705 H PhSO₂ CH₃ CF₃ B24 0 A706 H CH₃S CH₃ CF₃ B24 0 A707 H CH₃SO CH₃ CF₃ B24 0 A708 H CF₃ CH₃ CF₃ B24 0 A709 H F₂CH CH₃ CF₃ B24 0 A710 H HCC CH₃ CF₃ B24 0 A711 H CH₃CC CH₃ CF₃ B24 0 A712 H CH₂═CH CH₃ CF₃ B24 0 A713 H CH₂═CHCH₂ CH₃ CF₃ B24 0 A714 H CH₃SO₂N(CH₃) CH₃ CF₃ B24 0 A715 H (CH₃)₂N CH₃ CF₃ B24 0 A716 H (CH₃)₂NSO₂ CH₃ CF₃ B24 0 A717 H CH₃SCH₂ CH₃ CF₃ B24 0 A718 H CH₃SOCH₂ CH₃ CF₃ B24 0 A719 H CH₃SO₂CH₂ CH₃ CF₃ B24 0 A720 H CH₃ CH₃ CF₃CF₂ B24 0 A721 H CH₃CH₂ CH₃ CF₃CF₂ B24 0 A722 H cyclopropyl CH₃ CF₃CF₂ B24 0 A723 H (CH₃)₃C CH₃ CF₃CF₂ B24 0 A724 H (CH₃)₂CH CH₃ CF₃CF₂ B24 0 A725 H CH₃(CH₂)₂ CH₃ CF₃CF₂ B24 0 A726 H CH₃OCH₂ CH₃ CF₃CF₂ B24 0 A727 H CH₃O(CH₂)₂ CH₃ CF₃CF₂ B24 0 A728 H Ph CH₃ CF₃CF₂ B24 0 A729 H PhO CH₃ CF₃CF₂ B24 0 A730 H PhS CH₃ CF₃CF₂ B24 0 A731 H PhSO CH₃ CF₃CF₂ B24 0 A732 H PhSO₂ CH₃ CF₃CF₂ B24 0 A733 H CH₃S CH₃ CF₃CF₂ B24 0 A734 H CH₃SO CH₃ CF₃CF₂ B24 0 A735 H CF₃ CH₃ CF₃CF₂ B24 0 A736 H F₂CH CH₃ CF₃CF₂ B24 0 A737 H HCC CH₃ CF₃CF₂ B24 0 A738 H CH₃CC CH₃ CF₃CF₂ B24 0 A739 H CH₂═CH CH₃ CF₃CF₂ B24 0 A740 H CH₂═CHCH₂ CH₃ CF₃CF₂ B24 0 A741 H CH₃SO₂N(CH₃) CH₃ CF₃CF₂ B24 0 A742 H (CH₃)₂N CH₃ CF₃CF₂ B24 0 A743 H (CH₃)₂NSO₂ CH₃ CF₃CF₂ B24 0 A744 H CH₃SCH₂ CH₃ CF₃CF₂ B24 0 A745 H CH₃SOCH₂ CH₃ CF₃CF₂ B24 0 A746 H CH₃SO₂CH₂ CH₃ CF₃CF₂ B24 0 A747 H CH₃ CH₃ CF₃CF₂CF₂ B24 0 A748 H CH₃CH₂ CH₃ CF₃CF₂CF₂ B24 0 A749 H cyclopropyl CH₃ CF₃CF₂CF₂ B24 0 A750 H (CH₃)₃C CH₃ CF₃CF₂CF₂ B24 0 A751 H (CH₃)₂CH CH₃ CF₃CF₂CF₂ B24 0 A752 H CH₃(CH₂)₂ CH₃ CF₃CF₂CF₂ B24 0 A753 H CH₃OCH₂ CH₃ CF₃CF₂CF₂ B24 0 A754 H CH₃O(CH₂)₂ CH₃ CF₃CF₂CF₂ B24 0 A755 H Ph CH₃ CF₃CF₂CF₂ B24 0 A756 H PhO CH₃ CF₃CF₂CF₂ B24 0 A757 H PhS CH₃ CF₃CF₂CF₂ B24 0 A758 H PhSO CH₃ CF₃CF₂CF₂ B24 0 A759 H PhSO₂ CH₃ CF₃CF₂CF₂ B24 0 A760 H CH₃S CH₃ CF₃CF₂CF₂ B24 0 A761 H CH₃SO CH₃ CF₃CF₂CF₂ B24 0 A762 H CF₃ CH₃ CF₃CF₂CF₂ B24 0 A763 H F₂CH CH₃ CF₃CF₂CF₂ B24 0 A764 H HCC CH₃ CF₃CF₂CF₂ B24 0 A765 H CH₃CC CH₃ CF₃CF₂CF₂ B24 0 A766 H CH₂═CH CH₃ CF₃CF₂CF₂ B24 0 A767 H CH₂═CHCH₂ CH₃ CF₃CF₂CF₂ B24 0 A768 H CH₃SO₂N(CH₃) CH₃ CF₃CF₂CF₂ B24 0 A769 H (CH₃)₂N CH₃ CF₃CF₂CF₂ B24 0 A770 H (CH₃)₂NSO₂ CH₃ CF₃CF₂CF₂ B24 0 A771 H CH₃SCH₂ CH₃ CF₃CF₂CF₂ B24 0 A772 H CH₃SOCH₂ CH₃ CF₃CF₂CF₂ B24 0 A773 H CH₃SO₂CH₂ CH₃ CF₃CF₂CF₂ B24 0 A774 H CH₃ CH₃ CF₂Cl B24 0 A775 H CH₃CH₂ CH₃ CF₂Cl B24 0 A776 H cyclopropyl CH₃ CF₂Cl B24 0 A777 H (CH₃)₃C CH₃ CF₂Cl B24 0 A778 H (CH₃)₂CH CH₃ CF₂Cl B24 0 A779 H CH₃(CH₂)₂ CH₃ CF₂Cl B24 0 A780 H CH₃OCH₂ CH₃ CF₂Cl B24 0 A781 H CH₃O(CH₂)₂ CH₃ CF₂Cl B24 0 A782 H Ph CH₃ CF₂Cl B24 0 A783 H PhO CH₃ CF₂Cl B24 0 A784 H PhS CH₃ CF₂Cl B24 0 A785 H PhSO CH₃ CF₂Cl B24 0 A786 H PhSO₂ CH₃ CF₂Cl B24 0 A787 H CH₃S CH₃ CF₂Cl B24 0 A788 H CH₃SO CH₃ CF₂Cl B24 0 A789 H CF₃ CH₃ CF₂Cl B24 0 A790 H F₂CH CH₃ CF₂Cl B24 0 A791 H HCC CH₃ CF₂Cl B24 0 A792 H CH₃CC CH₃ CF₂Cl B24 0 A793 H CH₂═CH CH₃ CF₂Cl B24 0 A794 H CH₂═CHCH₂ CH₃ CF₂Cl B24 0 A795 H CH₃SO₂N(CH₃) CH₃ CF₂Cl B24 0 A796 H (CH₃)₂N CH₃ CF₂Cl B24 0 A797 H (CH₃)₂NSO₂ CH₃ CF₂Cl B24 0 A798 H CH₃SCH₂ CH₃ CF₂Cl B24 0 A799 H CH₃SOCH₂ CH₃ CF₂Cl B24 0 A800 H CH₃SO₂CH₂ CH₃ CF₂Cl B24 0 A801 H CH₃ CH₃ CHF₂ B24 0 A802 H CH₃CH₂ CH₃ CHF₂ B24 0 A803 H cyclopropyl CH₃ CHF₂ B24 0 A804 H (CH₃)₃C CH₃ CHF₂ B24 0 A805 H (CH₃)₂CH CH₃ CHF₂ B24 0 A806 H CH₃(CH₂)₂ CH₃ CHF₂ B24 0 A807 H CH₃OCH₂ CH₃ CHF₂ B24 0 A808 H CH₃O(CH₂)₂ CH₃ CHF₂ B24 0 A809 H Ph CH₃ CHF₂ B24 0 A810 H PhO CH₃ CHF₂ B24 0 A811 H PhS CH₃ CHF₂ B24 0 A812 H PhSO CH₃ CHF₂ B24 0 A813 H PhSO₂ CH₃ CHF₂ B24 0 A814 H CH₃S CH₃ CHF₂ B24 0 A815 H CH₃SO CH₃ CHF₂ B24 0 A816 H CF₃ CH₃ CHF₂ B24 0 A817 H F₂CH CH₃ CHF₂ B24 0 A818 H HCC CH₃ CHF₂ B24 0 A819 H CH₃CC CH₃ CHF₂ B24 0 A820 H CH₂═CH CH₃ CHF₂ B24 0 A821 H CH₂═CHCH₂ CH₃ CHF₂ B24 0 A822 H CH₃SO₂N(CH₃) CH₃ CHF₂ B24 0 A823 H (CH₃)₂N CH₃ CHF₂ B24 0 A824 H (CH₃)₂NSO₂ CH₃ CHF₂ B24 0 A825 H CH₃SCH₂ CH₃ CHF₂ B24 0 A826 H CH₃SOCH₂ CH₃ CHF₂ B24 0 A827 H CH₃SO₂CH₂ CH₃ CHF₂ B24 0 A828 H CH₃ CH₃ CCl₃ B24 0 A829 H CH₃CH₂ CH₃ CCl₃ B24 0 A830 H cyclopropyl CH₃ CCl₃ B24 0 A831 H (CH₃)₃C CH₃ CCl₃ B24 0 A832 H (CH₃)₂CH CH₃ CCl₃ B24 0 A833 H CH₃(CH₂)₂ CH₃ CCl₃ B24 0 A834 H CH₃OCH₂ CH₃ CCl₃ B24 0 A835 H CH₃O(CH₂)₂ CH₃ CCl₃ B24 0 A836 H Ph CH₃ CCl₃ B24 0 A837 H PhO CH₃ CCl₃ B24 0 A838 H PhS CH₃ CCl₃ B24 0 A839 H PhSO CH₃ CCl₃ B24 0 A840 H PhSO₂ CH₃ CCl₃ B24 0 A841 H CH₃S CH₃ CCl₃ B24 0 A842 H CH₃SO CH₃ CCl₃ B24 0 A843 H CF₃ CH₃ CCl₃ B24 0 A844 H F₂CH CH₃ CCl₃ B24 0 A845 H HCC CH₃ CCl₃ B24 0 A846 H CH₃CC CH₃ CCl₃ B24 0 A847 H CH₂═CH CH₃ CCl₃ B24 0 A848 H CH₂═CHCH₂ CH₃ CCl₃ B24 0 A849 H CH₃SO₂N(CH₃) CH₃ CCl₃ B24 0 A850 H (CH₃)₂N CH₃ CCl₃ B24 0 A851 H (CH₃)₂NSO₂ CH₃ CCl₃ B24 0 A852 H CH₃SCH₂ CH₃ CCl₃ B24 0 A853 H CH₃SOCH₂ CH₃ CCl₃ B24 0 A854 H CH₃SO₂CH₂ CH₃ CCl₃ B24 0 A855 H CH₃ Ph CF₃ B24 0 A856 H CH₃CH₂ Ph CF₃ B24 0 A857 H (CH₃)₂CH Ph CF₃ B24 0 A858 H (CH₃)₂CH Ph CF₃ B24 0 A859 H cyclopropyl Ph CF₃ B24 0 A860 H CH₃(CH₂)₂ Ph CF₃ B24 0 A861 H CH₃OCH₂ Ph CF₃ B24 0 A862 H CH₃O(CH₂)₂ Ph CF₃ B24 0 A863 H Ph Ph CF₃ B24 0 A864 H PhO Ph CF₃ B24 0 A865 H PhS Ph CF₃ B24 0 A866 H PhSO Ph CF₃ B24 0 A867 H PhSO₂ Ph CF₃ B24 0 A868 H CH₃S Ph CF₃ B24 0 A869 H CH₃SO Ph CF₃ B24 0 A870 H CF₃ Ph CF₃ B24 0 A871 H F₂CH Ph CF₃ B24 0 A872 H HCC Ph CF₃ B24 0 A873 H CH₃CC Ph CF₃ B24 0 A874 H CH₂═CH Ph CF₃ B24 0 A875 H CH₂═CHCH₂ Ph CF₃ B24 0 A876 H CH₃SO₂N(CH₃) Ph CF₃ B24 0 A877 H (CH₃)₂N Ph CF₃ B24 0 A878 H (CH₃)₂NSO₂ Ph CF₃ B24 0 A879 H CH₃SCH₂ Ph CF₃ B24 0 A880 H CH₃SOCH₂ Ph CF₃ B24 0 A881 H CH₃SO₂CH₂ Ph CF₃ B24 0 A882 H CH₃ Ph CF₃CF₂ B24 0 A883 H CH₃CH₂ Ph CF₃CF₂ B24 0 A884 H cyclopropyl Ph CF₃CF₂ B24 0 A885 H (CH₃)₃C Ph CF₃CF₂ B24 0 A886 H (CH₃)₂CH Ph CF₃CF₂ B24 0 A887 H CH₃(CH₂)₂ Ph CF₃CF₂ B24 0 A888 H CH₃OCH₂ Ph CF₃CF₂ B24 0 A889 H CH₃O(CH₂)₂ Ph CF₃CF₂ B24 0 A890 H Ph Ph CF₃CF₂ B24 0 A891 H PhO Ph CF₃CF₂ B24 0 A892 H PhS Ph CF₃CF₂ B24 0 A893 H PhSO Ph CF₃CF₂ B24 0 A894 H PhSO₂ Ph CF₃CF₂ B24 0 A895 H CH₃S Ph CF₃CF₂ B24 0 A896 H CH₃SO Ph CF₃CF₂ B24 0 A897 H CF₃ Ph CF₃CF₂ B24 0 A898 H F₂CH Ph CF₃CF₂ B24 0 A899 H HCC Ph CF₃CF₂ B24 0 A900 H CH₃CC Ph CF₃CF₂ B24 0 A901 H CH₂═CH Ph CF₃CF₂ B24 0 A902 H CH₂═CHCH₂ Ph CF₃CF₂ B24 0 A903 H CH₃SO₂N(CH₃) Ph CF₃CF₂ B24 0 A904 H (CH₃)₂N Ph CF₃CF₂ B24 0 A905 H (CH₃)₂NSO₂ Ph CF₃CF₂ B24 0 A906 H CH₃SCH₂ Ph CF₃CF₂ B24 0 A907 H CH₃SOCH₂ Ph CF₃CF₂ B24 0 A908 H CH₃SO₂CH₂ Ph CF₃CF₂ B24 0 A909 H CH₃ Ph CF₃CF₂CF₂ B24 0 A910 H CH₃CH₂ Ph CF₃CF₂CF₂ B24 0 A911 H cyclopropyl Ph CF₃CF₂CF₂ B24 0 A912 H (CH₃)₃C Ph CF₃CF₂CF₂ B24 0 A913 H (CH₃)₂CH Ph CF₃CF₂CF₂ B24 0 A914 H CH₃(CH₂)₂ Ph CF₃CF₂CF₂ B24 0 A915 H CH₃OCH₂ Ph CF₃CF₂CF₂ B24 0 A916 H CH₃O(CH₂)₂ Ph CF₃CF₂CF₂ B24 0 A917 H Ph Ph CF₃CF₂CF₂ B24 0 A918 H PhO Ph CF₃CF₂CF₂ B24 0 A919 H PhS Ph CF₃CF₂CF₂ B24 0 A920 H PhSO Ph CF₃CF₂CF₂ B24 0 A921 H PhSO₂ Ph CF₃CF₂CF₂ B24 0 A922 H CH₃S Ph CF₃CF₂CF₂ B24 0 A923 H CH₃SO Ph CF₃CF₂CF₂ B24 0 A924 H CF₃ Ph CF₃CF₂CF₂ B24 0 A925 H F₂CH Ph CF₃CF₂CF₂ B24 0 A926 H HCC Ph CF₃CF₂CF₂ B24 0 A927 H CH₃CC Ph CF₃CF₂CF₂ B24 0 A928 H CH₂═CH Ph CF₃CF₂CF₂ B24 0 A929 H CH₂═CHCH₂ Ph CF₃CF₂CF₂ B24 0 A930 H CH₃SO₂N(CH₃) Ph CF₃CF₂CF₂ B24 0 A931 H (CH₃)₂N Ph CF₃CF₂CF₂ B24 0 A932 H (CH₃)₂NSO₂ Ph CF₃CF₂CF₂ B24 0 A933 H CH₃SCH₂ Ph CF₃CF₂CF₂ B24 0 A934 H CH₃SOCH₂ Ph CF₃CF₂CF₂ B24 0 A935 H CH₃SO₂CH₂ Ph CF₃CF₂CF₂ B24 0 A936 H CH₃ Ph CF₂Cl B24 0 A937 H CH₃CH₂ Ph CF₂Cl B24 0 A938 H cyclopropyl Ph CF₂Cl B24 0 A939 H (CH₃)₃C Ph CF₂Cl B24 0 A940 H (CH₃)₂CH Ph CF₂Cl B24 0 A941 H CH₃(CH₂)₂ Ph CF₂Cl B24 0 A942 H CH₃OCH₂ Ph CF₂Cl B24 0 A943 H CH₃O(CH₂)₂ Ph CF₂Cl B24 0 A944 H Ph Ph CF₂Cl B24 0 A945 H PhO Ph CF₂Cl B24 0 A946 H PhS Ph CF₂Cl B24 0 A947 H PhSO Ph CF₂Cl B24 0 A948 H PhSO₂ Ph CF₂Cl B24 0 A949 H CH₃S Ph CF₂Cl B24 0 A950 H CH₃SO Ph CF₂Cl B24 0 A951 H CF₃ Ph CF₂Cl B24 0 A952 H F₂CH Ph CF₂Cl B24 0 A953 H HCC Ph CF₂Cl B24 0 A954 H CH₃CC Ph CF₂Cl B24 0 A955 H CH₂═CH Ph CF₂Cl B24 0 A956 H CH₂═CHCH₂ Ph CF₂Cl B24 0 A957 H CH₃SO₂N(CH₃) Ph CF₂Cl B24 0 A958 H (CH₃)₂N Ph CF₂Cl B24 0 A959 H (CH₃)₂NSO₂ Ph CF₂Cl B24 0 A960 H CH₃SCH₂ Ph CF₂Cl B24 0 A961 H CH₃SOCH₂ Ph CF₂Cl B24 0 A962 H CH₃SO₂CH₂ Ph CF₂Cl B24 0 A963 H CH₃ Ph CHF₂ B24 0 A964 H CH₃CH₂ Ph CHF₂ B24 0 A965 H (CH₃)₃C Ph CHF₂ B24 0 A966 H (CH₃)₂CH Ph CHF₂ B24 0 A967 H cyclopropyl Ph CHF₂ B24 0 A968 H CH₃(CH₂)₂ Ph CHF₂ B24 0 A969 H CH₃OCH₂ Ph CHF₂ B24 0 A970 H CH₃O(CH₂)₂ Ph CHF₂ B24 0 A971 H Ph Ph CHF₂ B24 0 A972 H PhO Ph CHF₂ B24 0 A973 H PhS Ph CHF₂ B24 0 A974 H PhSO Ph CHF₂ B24 0 A975 H PhSO₂ Ph CHF₂ B24 0 A976 H CH₃S Ph CHF₂ B24 0 A977 H CH₃SO Ph CHF₂ B24 0 A978 H CF₃ Ph CHF₂ B24 0 A979 H F₂CH Ph CHF₂ B24 0 A980 H HCC Ph CHF₂ B24 0 A981 H CH₃CC Ph CHF₂ B24 0 A982 H CH₂═CH Ph CHF₂ B24 0 A983 H CH₂═CHCH₂ Ph CHF₂ B24 0 A984 H CH₃SO₂N(CH₃) Ph CHF₂ B24 0 A985 H (CH₃)₂N Ph CHF₂ B24 0 A986 H (CH₃)₂NSO₂ Ph CHF₂ B24 0 A987 H CH₃SCH₂ Ph CHF₂ B24 0 A988 H CH₃SOCH₂ Ph CHF₂ B24 0 A989 H CH₃SO₂CH₂ Ph CHF₂ B24 0 A990 H CH₃ Ph CCl₃ B24 0 A991 H CH₃CH₂ Ph CCl₃ B24 0 A992 H (CH₃)₃C Ph CCl₃ B24 0 A993 H (CH₃)₂CH Ph CCl₃ B24 0 A994 H cyclopropyl Ph CCl₃ B24 0 A995 H CH₃(CH₂)₂ Ph CCl₃ B24 0 A996 H CH₃OCH₂ Ph CCl₃ B24 0 A997 H CH₃O(CH₂)₂ Ph CCl₃ B24 0 A998 H Ph Ph CCl₃ B24 0 A999 H PhO Ph CCl₃ B24 0 A1000 H PhS Ph CCl₃ B24 0 A1001 H PhSO Ph CCl₃ B24 0 A1002 H PhSO₂ Ph CCl₃ B24 0 A1003 H CH₃S Ph CCl₃ B24 0 A1004 H CH₃SO Ph CCl₃ B24 0 A1005 H CF₃ Ph CCl₃ B24 0 A1006 H F₂CH Ph CCl₃ B24 0 A1007 H HCC Ph CCl₃ B24 0 A1008 H CH₃CC Ph CCl₃ B24 0 A1009 H CH₂═CH Ph CCl₃ B24 0 A1010 H CH₂═CHCH₂ Ph CCl₃ B24 0 A1011 H CH₃SO₂N(CH₃) Ph CCl₃ B24 0 A1012 H (CH₃)₂N Ph CCl₃ B24 0 A1013 H (CH₃)₂NSO₂ Ph CCl₃ B24 0 A1014 H CH₃SCH₂ Ph CCl₃ B24 0 A1015 H CH₃SOCH₂ Ph CCl₃ B24 0 A1016 H CH₃SO₂CH₂ Ph CCl₃ B24 0 A1017 F H H CF₃ B24 0 A1018 Cl H H CF₃ B24 0 A1019 Br H H CF₃ B24 0 A1020 NC H H CF₃ B24 0 A1021 CH₃SO₂O H H CF₃ B24 0 A1022 CH₃O H H CF₃ B24 0 A1023 CH₃CH₂O H H CF₃ B24 0 A1024 CH₂CH═CH₂O H H CF₃ B24 0 A1025 HCCCH₂O H H CF₃ B24 0 A1026 PhCH₂S H H CF₃ B24 0 A1027 PhCH₂SO₂ H H CF₃ B24 0 A1028 ClCH₂CH₂ H H CF₃ B24 0 A1029 BrCH₂ H H CF₃ B24 0 A1030 FCH₂ H H CF₃ B24 0 A1031 CHF₂CH₂ H H CF₃ B24 0 A1032 CF₃CH₂ H H CF₃ B24 0 A1033 [1,3]-imidazol-1- H H CF₃ B24 0 ylmethyl A1034 CHCl₂CH₂ H H CF₃ B24 0 A1035 ClCH═CH H H CF₃ B24 0 A1036 Cl₂C═CH H H CF₃ B24 0 A1037 CF₃CH═CH H H CF₃ B24 0 A1038 ClCC H H CF₃ B24 0 A1039 PhCH₂ H H CF₃ B24 0 A1040 CH₃CH₂ CH₃ H CF₃ B24 0 A1041 CH₃ OH H CF₃ B24 0 A1042 CH₃ F H CF₃ B24 0 A1043 CH₃ Cl H CF₃ B24 0 A1044 F CH₃ H CF₃ B24 0 A1045 Cl CH₃ H CF₃ B24 0 A1046 H F H CF₃ B24 0 A1047 H Cl H CF₃ B24 0 A1048 H Br H CF₃ B24 0 A1049 H OH H CF₃ B24 0 A1050 H OCH₃ H CF₃ B24 0 A1051 H OCHF₂ H CF₃ B24 0 A1052 H OSO₂CH₃ H CF₃ B24 0 A1053 H OSO₂CF₃ H CF₃ B24 0 A1054 H ClCH₂ H CF₃ B24 0 A1055 H BrCH₂ H CF₃ B24 0 A1056 H FCH₂ H CF₃ B24 0 A1057 H CHF₂CH₂ H CF₃ B24 0 A1058 H CF₃CH₂ H CF₃ B24 0 A1059 H triazolylmethyl H CF₃ B24 0 A1060 H CHCl₂CH₂ H CF₃ B24 0 A1061 H ClCH═CH H CF₃ B24 0 A1062 H Cl₂C═CH H CF₃ B24 0 A1063 H CF₃CH═CH H CF₃ B24 0 A1064 H ClCC H CF₃ B24 0 A1065 H CH₃C(O) H CF₃ B24 0 A1066 H Ph H CF₃ B24 0 A1067 H SO₂CH₃ H CF₃ B24 0 A1068 H SO₂CF₃ H CF₃ B24 0 A1069 H NC H CF₃ B24 0 A1070 H NO₂ H CF₃ B24 0 A1071 CH₃ H F CF₃ B24 0 A1072 CH₃ H Cl CF₃ B24 0 A1073 CH₃ H Br CF₃ B24 0 A1074 CH₃ H NC CF₃ B24 0 A1075 CH₃ H CH₃O CF₃ B24 0 A1076 CH₃ H CH₃S CF₃ B24 0 A1077 CH₃ H CH₃SO CF₃ B24 0 A1078 CH₃ H CH₃SO₂ CF₃ B24 0 A1079 CH₃CH₂OCH₂ H H CF₃ B24 0 A1080 PhOCH₂ H H CF₃ B24 0 A1081

H H CF₃ B24 0 A1082 (CH₃)₂CH₂OCH₂ H H CF₃ B24 0 A1083 BrCH₂CH₂ H H CF₃ B24 0 A1084 FCH₂CH₂ H H CF₃ B24 0 A1085

H H CF₃ 0 A1086

H H CF₃ B24 0 A1087

H H CF₃ B24 0 A1088

H H CF₃ B24 0 A1089

H H CF₃ B24 0 A1090

H H CF₃ B24 0 A1091 cyclopropyl-CH₂ H H CF₃ B24 0 A1092 2,2-dichlorocycloprop- H H CF₃ B24 0 1-yl A1093 CH₃OC(O)CH═CH H H CF₃ B24 0 A1094 CH₃CH₂OC(O)CH═CH H H CF₃ B24 0 A1095 ClCH₂CH═CH H H CF₃ 0 A1096 CH═C═CH H H CF₃ B24 0 A1097 (CH₃)₂NCH₂ H H CF₃ B24 0 A1098 HOCH₂ H H CF₃ B24 0 A1099 CH₃C(O)OCH₂ H H CF₃ B24 0 A1100 PhC(O)OCH₂ H H CF₃ B24 0 A1101 PhCH₂CH₂ H H CF₃ B24 0 A1102 CH₃OC(O)CH₂ H H CF₃ B24 0 A1103 NCCH₂ H H CF₃ B24 0 A1104 CH₃(CH₂)₇SCH₂ H H CF₃ B24 0 A1105 CH₃(CH₂)₇SOCH₂ H H CF₃ B24 0 A1106 CH₃(CH₂)₇SO₂CH₂ H H CF₃ B24 0 A1107

H H CF₃ B24 0 A1108 ClCH₂CC H H CF₃ B24 0 A1109 CHF₂CH₂CH₂ H H CF₃ B24 0 A1110 CHCl₂CH₂CH₂ H H CF₃ B24 0 A1111 CF₃SO₂O H H CF₃ B24 0 A1112

H H CF₃ B24 0 A1113

H H CF₃ B24 0 A1114

H H CF₃ B24 0 A1115

H H CF₃ B24 0 A1116

H H CF₃ B24 0 A1117

H H CF₃ B24 0 A1118 CH₃ON═CHCH₂ H H CF₃ B24 0 A1119 O═CHCH₂ H H CF₃ B24 0 A1120 CH₃CH₂OCH₂ H H CF₂Cl B24 0 A1121 PhOCH₂ H H CF₂Cl B24 0 A1122

H H CF₂Cl B24 0 A1123 (CH₃)₂CH₂OCH₂ H H CF₂Cl B24 0 A1124 BrCH₂ H H CF₂Cl B24 0 A1125 FCH₂ H H CF₂Cl B24 0 A1126

H H CF₂Cl B24 0 A1127

H H CF₂Cl B24 0 A1128

H H CF₂Cl B24 0 A1129

H H CF₂Cl B24 0 A1130

H H CF₂Cl B24 0 A1131

H H CF₂Cl B24 0 A1132 cyclopropyl-CH₂ H H CF₂Cl B24 0 A1133 2,2-dichlorocycloprop- H H CF₂Cl B24 0 1-yl A1134 CH₃OC(O)CH═CH H H CF₂Cl B24 0 A1135 CH₃CH₂OC(O)CH═CH H H CF₂Cl B24 0 A1136 ClCH₂CH═CH H H CF₂Cl B24 0 A1137 CH═C═CH H H CF₂Cl B24 0 A1138 (CH₃)₂NCH₂ H H CF₂Cl B24 0 A1139 HOCH₂ H H CF₂Cl B24 0 A1140 CH₃C(O)OCH₂ H H CF₂Cl B24 0 A1141 PhC(O)OCH₂ H H CF₂Cl B24 0 A1142 PhCH₂ H H CF₂Cl B24 0 A1143 CH₃OC(O)CH₂ H H CF₂Cl B24 0 A1144 NCCH₂ H H CF₂Cl B24 0 A1145 CH₃(CH₂)₇SCH₂ H H CF₂C: B24 0 A1146 CH₃(CH₂)₇SOCH₂ H H CF₂Cl B24 0 A1147 CH₃(CH₂)₇SO₂CH₂ H H CF₂Cl B24 0 A1148

H H CF₂Cl B24 0 A1149 ClCH₂CC H H CF₂Cl B24 0 A1150 Br H H CF₂Cl B24 0 A1151 Cl H H CF₂Cl B24 0 A1152 CF₃SO₂O H H CF₂Cl B24 0 A1153

H H CF₂Cl B24 0 A1154

H H CF₂Cl B24 0 A1155

H H CF₂Cl B24 0 A1156

H H CF₂Cl B24 0 A1157

H H CF₂Cl B24 0 A1158

H H CF₂Cl B24 0 A1159 CH₃ON═CHCH₂ H H CF₂Cl B24 0 A1160 O═CHCH₂ H H CF₂Cl B24 0 A1161 CH₃CH₂OCH₂ H H CF₂H B24 0 A1162 PhOCH₂ H H CF₂H B24 0 A1163

H H CF₂H B24 0 A1164 (CH₃)₂CH₂OCH₂ H H CF₂H B24 0 A1165 BrCH₂ H H CF₂H B24 0 A1166 FCH₂ H H CF₂H B24 0 A1167

H H CF₂H B24 0 A1168

H H CF₂H B24 0 A1169

H H CF₂H B24 0 A1170

H H CF₂H B24 0 A1171

H H CF₂H B24 0 A1172

H H CF₂H B24 0 A1173 cyclopropyl-CH₂ H H CF₂H B24 0 A1174 2,2-dichlorocycloprop- H H CF₂H B24 0 1-yl A1175 CH₃OC(O)CH═CH H H CF₂H B24 0 A1176 CH₃CH₂OC(O)CH═CH H H CF₂H B24 0 A1177 ClCH₂CH═CH H H CF₂H B24 0 A1178 CH═C═CH H H CF₂H B24 0 A1179 (CH₃)₂NCH₂ H H CF₂H B24 0 A1180 HOCH₂ H H CF₂H B24 0 A1181 CH₃C(O)OCH₂ H H CF₂H B24 0 A1182 PhC(O)OCH₂ H H CF₂H B24 0 A1183 PhCH₂ H H CF₂H B24 0 A1184 CH₃OC(O)CH₂ H H CF₂H B24 0 A1185 NCCH₂ H H CF₂H B24 0 A1186 CH₃(CH₂)₇SCH₂ H H CF₂H B24 0 A1187 CH₃(CH₂)₇SOCH₂ H H CF₂H B24 0 A1188 CH₃(CH₂)₇SO₂CH₂ H H CF₂H B24 0 A1189

H H CF₂H B24 0 A1190 ClCH₂CC H H CF₂H B24 0 A1191 Br H H CF₂H B24 0 A1192 Cl H H CF₂H B24 0 A1193 CF₃SO₂O H H CF₂H B24 0 A1194

H H CF₂H B24 0 A1195

H H CF₂H B24 0 A1196

H H CF₂H B24 0 A1197

H H CF₂H B24 0 A1198

H H CF₂H B24 0 A1199

H H CF₂H B24 0 A1200 CH₃ON═CHCH₂ H H CF₂H B24 0 A1201 O═CHCH₂ H H CF₂H B24 0 A1202 CH₃CH═CH H H CF₃ B24 0 A1203 CH₃SO₂NH H H CF₃ B24 0 A1204 CH₃CH₂CH₂O H CH₃ CF₃ B24 0 A1205 Cl CH₃ H CF₃ B24 0 A1206 F₂CHO H H CF₃ B24 0 A1207 CH₃CH₂C(O)OCH₂ H H CF₃ B24 0 A1208 CH₃CH₂OC(O)OCH₂ H H CF₃ B24 0 A1209 CH₃OCH₂OCH₂ H H CF₃ B24 0 A1210 CH₃ H H CF₃ B24 1 A1211 CH₃CH₂ H H CF₃ B24 1 A1212 cyclopropyl H H CF₃ B24 1 A1213 CH₃(CH₂)₂ H H CF₃ B24 1 A1214 CH₃OCH₂ H H CF₃ B24 1 A1215 CF₃ H H CF₃ B24 1 A1216 F₂CH H H CF₃ B24 1 A1217 ClCH₂ H H CF₃ B24 1 A1218 CH₃SO₂CH₂ H H CF₃ B24 1 A1219 CH₃ CF₃ H CH₃ B24 1 A1220 CH₃CH₂OCH₂ H H CF₃ B24 1 A1221 PhOCH₂ H H CF₃ B24 1 A1222 (CH₃)₂CH₂OCH₂ H H CF₃ B24 1 A1223 BrCH₂ H H CF₃ B24 1 A1224 FCH₂ H H CF₃ B24 1 A1225

H H CF₃ B24 1 A1226

H H CF₃ B24 1 A1227 cyclopropyl-CH₂ H H CF₃ B24 1 A1228 2,2-dichlorocycloprop- H H CF₃ B24 1 1-yl A1229 (CH₃)₂NCH₂ H H CF₃ B24 1 A1230 HOCH₂ H H CF₃ B24 1 A1231 CH₃C(O)OCH₂ H H CF₃ B24 1 A1232 PhC(O)OCH₂ H H CF₃ B24 1 A1233 PhCH₂ H H CF₃ B24 1 A1234 CH₃OC(O)CH₂ H H CF₃ B24 1 A1235 NCCH₂ H H CF₃ B24 1 A1236 CH₃(CH₂)₇SO₂CH₂ H H CF₃ B24 1 A1237 Br H H CF₃ B24 1 A1238 Cl H H CF₃ B24 1 A1239 O═CHCH₂ H H CF₃ B24 1 A1240 CH₃ H H CF₂Cl B24 1 A1241 CH₃CH₂ H H CF₂Cl B24 1 A1242 cyclopropyl H H CF₂Cl B24 1 A1243 CH₃(CH₂)₂ H H CF₂Cl B24 1 A1244 CH₃OCH₂ H H CF₂Cl B24 1 A1245 CF₃ H H CF₂Cl B24 1 A1246 F₂CH H H CF₂Cl B24 1 A1247 ClCH₂ H H CF₂Cl B24 1 A1248 CH₃SO₂CH₂ H H CF₂Cl B24 1 A1249 CH₃ CF₃ H CF₂Cl B24 1 A1250 CH₃CH₂OCH₂ H H CF₂Cl B24 1 A1251 PhOCH₂ H H CF₂Cl B24 1 A1252 (CH₃)₂CH₂OCH₂ H H CF₂Cl B24 1 A1253 BrCH₂ H H CF₂Cl B24 1 A1254 FCH₂ H H CF₂Cl B24 1 A1255

H H CF₂Cl B24 1 A1256

H H CF₂Cl B24 1 A1257 cyclopropyl-CH₂ H H CF₂Cl B24 1 A1258 2,2-dichlorocycloprop- H H CF₂Cl B24 1 1-yl A1259 (CH₃)₂NCH₂ H H CF₂Cl B24 1 A1260 HOCH₂ H H CF₂Cl B24 1 A1261 CH₃C(O)OCH₂ H H CF₂Cl B24 1 A1262 PhC(O)OCH₂ H H CF₂Cl B24 1 A1263 PhCH₂ H H CF₂Cl B24 1 A1264 CH₃OC(O)CH₂ H H CF₂Cl B24 1 A1265 NCCH₂ H H CF₂Cl B24 1 A1266 CH₃(CH₂)₇SO₂CH₂ H H CF₂Cl B24 1 A1267 Br H H CF₂Cl B24 1 A1268 Cl H H CF₂Cl B24 1 A1269 O═CHCH₂ H H CF₂Cl B24 1 A1270 CH₃ H H CF₂H B24 1 A1271 CH₃CH₂ H H CF₂H B24 1 A1272 cyclopropyl H H CF₂H B24 1 A1273 CH₃(CH₂)₂ H H CF₂H B24 1 A1274 CH₃OCH₂ H H CF₂H B24 1 A1275 CF₃ H H CF₂H B24 1 A1276 F₂CH H H CF₂H B24 1 A1277 ClCH₂ H H CF₂H B24 1 A1278 CH₃SO₂CH₂ H H CF₂H B24 1 A1279 CH₃ CF₃ H CF₂H B24 1 A1280 CH₃CH₂OCH₂ H H CF₂H B24 1 A1281 PhOCH₂ H H CF₂H B24 1 A1282 (CH₃)₂CH₂OCH₂ H H CF₂H B24 1 A1283 BrCH₂ H H CF₂H B24 1 A1284 FCH₂ H H CF₂H B24 1 A1285

H H CF₂H B24 1 A1286

H H CF₂H B24 1 A1287 cyclopropyl-CH₂ H H CF₂H B24 1 A1288 2,2-dichlorocycloprop- H H CF₂H B24 1 1-yl A1289 (CH₃)₂NCH₂ H H CF₂H B24 1 A1290 HOCH₂ H H CF₂H B24 1 A1291 CH₃C(O)OCH₂ H H CF₂H B24 1 A1292 PhC(O)OCH₂ H H CF₂H B24 1 A1293 PhCH₂ H H CF₂H B24 1 A1294 CH₃OC(O)CH₂ H H CF₂H B24 1 A1295 NCCH₂ H H CF₂H B24 1 A1296 CH₃(CH₂)₇SO₂CH₂ H H CF₂H B24 1 A1297 Br H H CF₂H B24 1 A1298 Cl H H CF₂H B24 1 A1299 O═CHCH₂ H H CF₂H B24 1 A1300 CH₃ H H CF₃CF₂ B24 1 A1301 HO H Ph CF₃ B24 0 A1302 CH₃ H CH₂═CH CF₃ B24 0 A1303 CH₃ H CH₃CH₂O CF₃ B24 0 A1304 HO CH₃ H CF₃ B24 0 A1305 HO H H CF₃ B24 0 A1306 (CH₃CH₂)₂N(O)CO H H CF₃ B24 0 A1307 CH₃ H tosyl-O CF₃ B24 0 A1308 CH₃ H CH₃CC CF₃ B24 0 A1309 CH₃ H HCC CF₃ B24 0 A1310 CH₃ H ClCH₂CC CF₃ B24 0 A1311 CH₃ H PhCH₂O CF₃ B24 0 A1312 CH₃ H CF₃SO₂O CF₃ B24 0 A1313 CH₃ H (CH₃)₂N CF₃ B24 0 A1314 CH₃ H CH₃C(O)O CF₃ B24 0 A1315 CH₃ H CH₃CH₂C(O) CF₃ B24 0 O A1316 CH₃ H PhC(O)O CF₃ B24 0 A1317 CH₃ H 3-pyridyl CF₃ B24 0 A1318 CH₃OCH₂OCH₂ H H CF₂Cl B24 0 A1319 CH₃OCH₂OCH₂ H H CF₂H B24 0 A1320 CH₃OCH₂OCH₂ H H CF₂CF₃ B24 0 A1321 CH₃OCH₂OCH₂ H H CF₃ B24 1 A1322 CH₃O H CH₃ CF₃ B24 0

In the formulaic representations of the tables (for example Table 7, compound A 1088, substituent R₂), the linkage site with the pyridine ring is on the right-hand side of the formulaic representation. Terminal valencies are a methyl group.

TABLE 8 Compounds of the formula Ib (p is 0 or 1): (Ib)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B786 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 9 Compounds of the formula Ic (p is 0 or 1): (Ic)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B4B1 B4B2 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B556 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 10 Compounds of the formula Id (p is 0 or 1): (Id)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B4B2 B4B3 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 11 Compounds of the formula Ie (p is 0 or 1): (Ie)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B2 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B452 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B4B7 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 12 Compounds of the formula If (p is 0 or 1): (If)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1056 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1685 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 13 Compounds of the formula Ig (p is 0 or 1): (Ig)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B312 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B401 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B&40 B641 B642 B643 B644 B645 B646 B647 B648 B649 B659 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 14 Compounds of the formula Ih (p is 0 or 1): (Ih)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B4B1 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 15 Compounds of the formula Ik (p is 0 or 1): (Ik)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B1Y B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 16 Compounds of the formula Im (p is 0 or 1): (Im)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15 B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B440 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B4B2 B4B3 B4B4 B4B5 B4B6 B4B7 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B775 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 17 Compounds of the formula In (p is 0 or 1): (In)

Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ Q₁ B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12 B13 B14 B15, B16 B17 B18 B19 B20 B21 B22 B23 — B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36 B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48 B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60 B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72 B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84 B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96 B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108 B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120 B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144 B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168 B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180 B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192 B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204 B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216 B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252 B253 B254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264 B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276 B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 B290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300 B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312 B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324 B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336 B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348 B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360 B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396 B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444 B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B4B6 B487 B488 B489 B490 B491 B492 B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564 B565 B566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588 B589 B590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600 B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636 B637 B638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648 B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904 B905 B906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916 B917 B918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1098 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1197 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217

TABLE 18 Compounds of the formula Io (p is 0 or 1): (Io)

Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35 C36 C37 C38 C39 C40 C41 C42 C43 C44 C45 C46 C47 C48 C49 C50 C51 C52 C53 C54 C55 C56 C57 C58 C59 C60 C61 C62 C63 C64 C65 C66 C67 C68 C69 C70 C71 C72 C73 C74 C75 C76 C77 C78 C79 C80 C81 C82 C83 C84 C85 C86 C87 C88 C89 C90 C91 C92 C93 C94 C95 C96 C97 C98 C99 C100 C101 C102 C103 C104 C105 C106 C107 C108 C109 C110 C111 C112 C113 C114 C115 C116 C117 C118 C119 C120 C121 C122 C123 C124 C125 C126 C127 C128 C129 C130 C131 C132 C133 C134 C135 C136 C137 C138 C139 C140 C141 C142 C143 C144 C145 C146 C147 C148 C149 C150 C151

TABLE 19 Compounds of the formula Iq (p is 0 or 1): (Iq)

Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ Q₂ C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35 C36 C37 C38 C39 C40 C41 C42 C43 C44 C45 C46 C47 C48 C49 C50 C51 C52 C53 C54 C55 C56 C57 C58 C59 C60 C61 C62 C63 C64 C65 C66 C67 C68 C69 C70 C71 C72 C73 C74 C75 C76 C77 C78 C79 C80 C81 C82 C83 C84 C85 C86 C87 C88 C89 C90 C91 C92 C93 C94 C95 C96 C97 C98 C99 C100 C101 C102 C103 C104 C105 C106 C107 C108 C109 C110 C111 C112 C113 C114 C115 C116 C117 C118 C119 C120 C121 C122 C123 C124 C125 C126 C127 C128 C129 C130 C131 C132 C133 C134 C135 C136 C137 C138 C139 C140 C141 C142 C143 C144 C145 C146 C147 C148 C149 C150 C151

TABLE 20 Compounds of the formula Ir (p is 0 or 1): (Ir)

Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ D1 D2 D3 D4 D5 D6 D7 D8 D9 D10 D11 D12 D13 D14 D15 D16 D17 D18 D19 D20 D21 D22 D23 D24 D25 D26 D27 D28 D29 D30 D31 D32 D33 D34 D35 D36 D37 D38 D39 D40 D41 D42 D43 D44 D45 D46 D47 D48 D49 D50 D51 D52 D53 D54 D55 D56 D57 D58 D59 D60 D61 D62 D63 D64 D65 D66 D67 D68 D69 D70 D71 D72 D73 D74 D75 D76 D77 D78 D79 D80 D81 D82 D83 D84 D85 D86 D87 D88 D89 D90 D91 D92 D93 D94 D95 D96 D97 D98 D99 D100 D101 D102 D103 D104 D105 D106 D107 D108 D109 D110 D111 D112 D113 D114 D115 D116 D117 D118 D119 D120 D121 D122 D123 D124 D125 D126 D127 D128 D129 D130 D131 D132 D133 D134 D135 D136 D137 D138 D139 D140

TABLE 21 Compounds of the formula Is (p is 0 or 1): (Is)

Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ Q₃ D1 D2 D3 D4 D5 D6 D7 D8 D9 D10 D11 D12 D13 D14 D15 D16 D17 D18 D19 D20 D21 D22 D23 D24 D25 D26 D27 D28 D29 D30 D31 D32 D33 D34 D35 D36 D37 D38 D39 D40 D41 D42 D43 D44 D45 D46 D47 D48 D49 D50 D51 D52 D53 D54 D55 D56 D57 D58 D59 D60 D61 D62 D63 D64 D65 D66 D67 D68 D69 D70 D71 D72 D73 D74 D75 D76 D77 D78 D79 D80 D81 D82 D83 D84 D85 D86 D87 D88 D89 D90 D91 D92 D93 D94 D95 D96 D97 D98 D99 D100 D101 D102 D103 D104 D105 D106 D107 D108 D109 D110 D111 D112 D113 D114 D115 D116 D117 D118 D119 D120 D121 D122 D123 D124 D125 D126 D127 D128 D129 D130 D131 D132 D133 D134 D135 D136 D137 D138 D139 D140

TABLE 22 Compounds of the formula It (p is 0 or 1): (It)

Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ E1 E2 E3 E4 E5 E6 E7 E8 E9 E10 E11 E12 E13 E14 E15 E16 E17 E18 E19 E20 E21 E22 E23 E24 E25 E26 E27 E28 E29 E30

TABLE 23 Compounds of the formula Iu (p is 0 or 1); (Iu)

Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ Q₄ E1 E2 E3 E4 E5 E6 E7 E8 E9 E10 E11 E12 E13 E14 E15 E16 E17 E18 E19 E20 E21 E22 E23 E24 E25 E26 E27 E28 E29 E30

TABLE 24 Compounds of the formula Iv (p is 0 or 1): (Iv)

Q₅ Q₅ Q₅ Q₅ Q₅ Q₅ F1 F2 F3 F4 F5 F6

TABLE 25 Compounds of the formula Iw (P is 0 or 1): (Iw)

Q₅ Q₅ Q₅ Q₅ Q₅ Q₅ F1 F2 F3 F4 F5 F6

TABLE 26 Physical data of the intermediates: Melting points are indicated in ° C. Compound Phys. dat. Compound Phys. dat. A17  99-100 A1025 crystalline A7 105-106 A1206 94-95 A9 73-74 A1022 oil A6 148-150 A1203 crystalline A26 143-144 A21 amorphous A34 170-171 A1023 110-111 A1026 crystalline A1085 188-191 A1304 crystalline A1088 157-158 A1301 crystalline A1092 crystalline A1018 110-111 A1095 136-138 A1 195-197 A1096 194-196 A2 150-151 A124 135-136 A15 164-166 A31 209-210 A27 107-108 H-B1057 166-167 A29 173-174 H-B1058 crystalline A32 145-146 H-B1061 crystalline A30 178-181 H-B1063 crystalline A4 143-144 H-B1065 oil A3 148-149 H-B1066 150-152 A10 166-167 H-B1067 122-123 A8 123-124 H-B1069 117-118 A5 81-82 H-B1070 crystalline A154 108-110 H-C1 116-118 A64 134-135 H-C24 172-175 A94 134-135 A1205 crystalline A531 crystalline H-D113 oil A1045 crystalline H-F5 oil A1322 crystalline H-E16 145-148 A184 146-147 A1088 157-158 A358 155-156 A1103 152-153

TABLE 27 Physical data for the compounds of the formula I indicated in the above tables: (The melting points are indicated in ° C.) Comp. No. m.p. Phys. state Comp. No. m.p. Phys. state A2-B1 90-92 crystalline A34-B1 53-54 crystalline A2-B1082 — resin A9-B1 — oil A2-B1083 — resin A184-B1 98-99 crystalline A2-B90 — resin A184-B24 101-102 crystalline A2-B68 120-121 crystalline A7-B24 — oil A2-B24 75-76 crystalline A3-B24 — oil A7-B1 — oil A34-B24 51-52 crystalline A2-B73 — resin A2-B1091 — oil A2-B75 — amorphous A2-B1092 — oil A2-B95 106-107 crystalline A8-B24 52-53 crystalline A2-B93 95-96 crystalline A18-B24 — oil A8-B1 97-98 crystalline A2-B552 — resin A2-B925 — oil A2-C152 — oil A3-B1 42-44 crystalline A2-B69 — resin A94-B1 57-58 crystalline A2-D36 — resin A2-B1057 — amorphous A2-B618 — resin A2-B1063 — oil A2-B49 — resin A2-B1061 — oil A2-D71 — resin A2-B133 58-60 crystalline A2-B1093 — resin A2-B1058 89-91 crystalline A2-B26 — oil A64-B24 80-82 crystalline A2-B33 — resin A64-B1 49-51 crystalline A2-B34 — waxy A2-B1089 — oil A2-B35 — waxy A2-B31 151-153 crystalline A2-B1087 — viscous A2-B1090 139-140 crystalline A2-B1094 — viscous A154-B1 94-95 crystalline A2-B1088 108-109 crystalline A2-B46(cis) 61-62 crystalline A531-B24 — viscous A2-B46(trans) 83-84 crystalline A2-B1099 94-96 crystalline A2-B91 — resin A2-B1095 — viscous A2-B2 — resin A2-B1097 — oil A2-B29 87-88 crystalline A2-B1098 92-93 crystalline A2-B1066 — viscous A2-C147 — resin A2-B25 — oil A2-B70 — resin A2-B1067 — resin A2-B49 — resin A2-B1069 — oil A2-C1 — oil A2-B1068 — viscous A2-B1096 — resin A2-B1070 — viscous A2-B1085 176-177 crystalline A2-B5 — resin A1022-B24 — oil A2-C149 — resin A2-C47 107-110 crystalline A2-C146 — oil A2-B1100 128-130 crystalline A2-B112 — resin A8-B2 70-71 crystalline A2-D140 — oil A8-B1064 — resin A2-B354 139-140 crystalline A2-B45 — resin A2-E16 — solid A2-B10 — viscous A6-B1 123-124 crystalline A8-B133 68-69 crystalline A6-B24 — oil A8-B1101 113-114 crystalline A1322-B24 — oil A8-B1106 — oil A2-B1101 124-125 crystalline A2-D111(trans) — oil A2-B156 — oil A2-D111(cis) — resin A2-B144 — resin A8-D111(trans) — oil A2-B145 — resin A8-D109 62-62 amorphous A2-B134 — resin A8-B35 — oil A1210-B354 220 crystalline A1023-B2 — resin A2-C2 — oil A1023-B354 95-97 crystalline A358-B1 — oil A15-B354 — resin A2-D36 — resin A8-B354 — oil A1208-B354 — oil A8-B1067 — oil A2-D113(Isom. A) — oil A8-C146 — oil A2-D113(Isom. B) — oil A8-C1 — oil A2-D114(Isom. A) 159-160 crystalline A94-B34 108-110 crystalline A2-D115 — amorphous A94-B35 82-84 crystalline A1025-B354 — viscous A1210-B354 — amorphous A2-B1102 124-125 crystalline A2-B1105 119 crystalline A2-B1104 165-167 crystalline A1099-B1107 — amorphous A1210-B1 117-119 crystalline A2-B1123 — resin A8-B34 — oil A8-B1123 — resin A8-B1103 — oil A2-B1138 — resin A8-B1063 90-92 crystalline A124-B1 60-65 crystalline A8-B29 — oil A1170-B1 106-107 crystalline A2-C24 — oil A124-B34 — oil A8-B552 — oil A124-B35 — oil A8-B156 — resin A94-B2 53-57 crystalline A1210-B1105 145-146 glassy- A2-B1174 — crystalline amorphous A1206-B354 — amorphous A2-B1213 133-134 crystalline A8-B134 — oil A3-B1213 — oil A8-D36 — oil A4-B1213 — oil A8-B1213 71-72 crystalline A2-B1214 — resin A8-F5 — resin A2-F5 — resin A1029-B1105 94.5-95   crystalline A2-D109 — oil

BIOLOGICAL EXAMPLES Example B1 Herbicidal Action Before Emergence of the Plants (Pre-emergence Action)

Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic pots. Immediately after sowing, the test substances as aqueous suspensions (prepared with a 25% wettable powder (Example F3, b) in accordance with WO 97/34485) or as emulsions (prepared with a 25% emulsion concentrate (Example F1, c)) are sprayed on at a rate of 2 kg of a.i./ha or 250 g of a.i./ha (500 l of water/ha). The test plants are then grown in the greenhouse under optimal conditions. After a test period of 3 weeks, the experiment is evaluated with reference to a nine-step scale (1=complete damage, 9=no effect). Score figures of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action.

TABLE B1a pre-emergence action Compound g/ha Cyperus Ipomoea Setaria Sinapis Solanum Stellaria A2-B1 2000 2 2 1 2 2 1 A2-B1082 2000 2 2 2 2 1 2 A2-B1083 2000 2 3 3 4 2 3 A2-B90 2000 1 1 1 1 1 1 A2-B68 2000 1 2 1 2 1 2 A2-B24 2000 1 1 1 2 1 1 A2-B73 2000 3 4 2 2 2 2 A2-B75 2000 2 3 2 2 1 2 A2-B95 2000 2 4 2 2 1 2 A2-B93 2000 2 4 2 2 1 2 A3-B1 2000 2 2 4 2 3 2 A94-B1 2000 1 2 2 1 1 2 A2-B1063 2000 1 2 1 2 1 2 A2-B1061 2000 3 3 2 2 1 2 A2-B133 2000 1 2 2 2 1 2 A64-B24 2000 4 4 2 2 1 2 A2-B1089 2000 1 2 2 2 1 2 A2-B31 2000 2 3 4 2 1 2 A2-B46(cis) 2000 1 2 1 2 1 2 A2-B46(trans) 2000 1 2 1 2 1 2 A2-B91 2000 1 2 1 2 1 2 A2-B2 2000 1 1 1 1 1 2 A2-B25 2000 2 3 2 2 1 2 A2-B1067 2000 2 3 2 2 3 3 A2-B1068 2000 2 2 2 2 1 2 A2-B1070 2000 2 3 3 2 2 2 A2-C146 2000 1 2 2 2 1 2 A2-B354 2000 1 1 1 1 1 2 A34-B1 2000 1 2 2 2 2 3 A9-B1 2000 2 1 2 1 1 2 A184-B1 2000 2 4 2 2 1 2 A184-B24 2000 1 3 2 2 1 2 A3-B24 2000 1 3 2 2 1 2 A8-B24 2000 1 2 2 2 1 3 A18-B24 2000 1 1 1 1 1 2 A2-B552 2000 1 2 2 2 1 2 A2-C152 2000 1 1 2 2 1 2 A2-B69 2000 1 4 2 2 1 1 A2-D36 2000 1 2 2 2 1 1 A2-B618 2000 1 1 1 2 1 1 A2-B33 2000 1 3 2 2 1 3 A2-B34 2000 1 3 2 2 1 2 A2-B35 2000 2 4 2 2 2 2 A2-B1095 2000 3 4 2 2 1 2 A2-C147 2000 2 4 2 2 2 2 A2-B49 2000 2 4 2 2 1 2 A2-C1 2000 2 3 1 2 1 2 A2-B1100 2000 1 3 1 2 1 2 A8-B2 2000 1 3 2 2 1 2 A8-B1064 2000 2 4 3 2 1 3 A8-B1101 2000 2 4 2 2 1 1 A2-B156 2000 1 2 1 2 1 2 A2-B144 2000 3 4 2 2 2 4 A2-B134 2000 1 2 1 2 1 1 A1210-B354 2000 2 3 2 1 1 2 A2-C2 2000 2 3 1 1 1 1 A2-D36 2000 1 2 1 2 3 1 A2-D113(Isom. A) 2000 4 4 2 1 3 3 A2-D115 2000 3 3 2 2 2 3 AB-B34 2000 2 3 2 2 2 2 AB-B1103 2000 1 3 2 1 1 2 A2-C24 2000 1 2 1 1 1 2

TABLE B1b Pre-emergence action: Compound g/ha Panicum Digitaria Echino. Abutilon Amaranthus Chenop. A8-B1 250 2 2 2 1 1 1 A1022-B24 250 2 4 4 3 4 1 A2-B145 250 2 2 4 2 3 1 A1208-B364 250 1 1 1 1 1 1 A8-B1063 250 2 3 3 2 4 1 A8-B552 250 2 3 4 1 4 1 A8-B156 250 3 3 3 3 4 2 A1210-B1105 250 2 3 2 1 4 1

The same results are obtained when the compounds of the formula I are formulated in accordance with Examples F2 and F4 to F8 in accordance with WO 97/34485.

Example B2 Post-emergence Herbicidal Action

Monocotyledonous and dicotyledonous test plants are grown in the greenhouse in plastic pots containing standard soil, and, in the 4- to 6-leaf stage, sprayed with an aqueous suspension of the test substances of the formula I prepared with a 25% wettable powder (Example F3, b) in accordance with WO 97/34485) or with an emulsion of the test substances of the formula I prepared with a 25% emulsion concentrate (Example F1, c) in accordance with WO 97/34485), corresponding to a rate of 2 kg of a.i./ha or 250 g of a.i./ha (500 l of water/ha). The test plants are subsequently grown on in the greenhouse under optimal conditions. After a test period of approximately 18 days, the test is evaluated; with reference to a nine-step scale (1=complete damage, 9=no effect). Score figures of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action. In this test, the compounds of the formula I show a potent herbicidal action.

TABLE B2a Post-emergence action: Compound g/ha Ipomoea Lolium Setaria Sinapis Solanum Stellaria A2-B1 2000 1 2 1 1 1 2 A2-B1082 2000 1 2 2 1 1 2 A2-B1083 2000 1 4 2 1 1 2 A2-B90 2000 1 2 2 1 2 2 A2-B68 2000 1 2 2 1 1 2 A2-B24 2000 1 2 2 1 2 2 A2-B73 2000 1 3 2 1 1 2 A2-B75 2000 2 2 3 1 2 2 A2-B95 2000 1 2 2 1 2 2 A2-B93 2000 1 2 2 1 2 2 A3-B1 2000 1 3 2 1 1 2 A94-B1 2000 1 2 2 1 1 1 A2-B1063 2000 2 2 4 1 2 2 A2-B1061 2000 2 2 2 1 2 2 A2-B133 2000 1 2 2 1 2 2 A2-B1058 2000 1 2 4 1 2 2 A64-B24 2000 2 2 4 1 2 2 A64-B1 2000 2 3 4 1 1 2 A2-B1089 2000 1 2 2 1 1 2 A2-B31 2000 2 2 2 1 2 2 A2-B1090 2000 2 4 4 2 2 2 A2-B46(cis) 2000 1 2 3 1 2 2 A2-B46(trans) 2000 1 2 2 1 1 2 A2-B91 2000 1 2 2 1 2 2 A2-B2 2000 1 2 2 1 2 2 A2-B29 2000 2 3 2 1 2 2 A2-B1066 2000 1 3 2 1 2 2 A2-B25 2000 1 2 2 2 1 2 A2-B1068 2000 1 2 4 1 1 2 A2-B1070 2000 2 4 2 2 2 2 A2-B5 2000 1 2 2 1 2 2 A2-C149 2000 1 3 2 1 2 2 A2-C146 2000 1 2 2 1 2 2 A2-B112 2000 2 3 2 1 2 2 A2-B354 2000 2 2 2 2 2 2 A2-E16 2000 2 3 2 2 2 2 A6-B24 2000 1 3 2 1 1 2 A34-B1 2000 1 2 2 1 1 2 A9-B1 2000 2 4 2 2 2 2 A184-B1 2000 1 3 2 1 2 2 A184-B24 2000 1 2 2 1 2 2 A7-B24 2000 1 2 2 1 2 2 A3-B24 2000 2 2 2 1 2 2 A34-B24 2000 1 2 2 1 2 2 A8-B24 2000 2 2 2 1 2 2 A18-B24 2000 1 2 2 1 2 2 A2-C152 2000 2 2 3 1 2 2 A2-B69 2000 1 2 2 1 2 2 A2-D36 2000 2 2 2 1 2 2 A2-B618 2000 2 2 2 1 2 2 A2-B49 2000 2 2 2 1 2 2 A2-B1093 2000 2 2 2 1 2 2 A2-B33 2000 2 4 2 1 2 2 A2-B34 2000 1 3 2 1 1 2 A2-B35 2000 1 3 2 1 1 2 A2-B1087 2000 1 4 3 1 2 2 A531-B24 2000 2 2 2 1 2 2 A2-B1095 2000 1 2 4 1 2 2 A2-C147 2000 1 2 2 1 2 2 A2-B70 2000 3 4 3 1 2 2 A2-B49 2000 2 2 2 1 2 2 A2-C1 2000 3 2 2 1 2 2 A2-B1100 2000 2 2 3 1 1 2 A8-B2 2000 2 2 2 2 2 3 A8-B1064 2000 2 4 2 1 1 2 A8-B133 2000 2 4 2 1 2 2 A8-B1101 2000 2 3 2 1 2 2 A2-B1101 2000 2 2 2 1 1 3 A2-B156 2000 1 2 2 1 2 2 A2-B134 2000 2 2 1 1 1 2 A1210-B354 2000 2 2 2 1 1 2 A2-C2 2000 2 1 1 1 1 1 A2-D36 2000 2 1 1 1 1 1 A2-D113(Isom. A) 2000 2 1 1 1 1 2 A2-D113(Isom. B) 2000 2 2 2 2 1 2 A2-D114 2000 2 1 1 1 1 1 A2-D115 2000 1 2 1 1 1 1 A8-B34 2000 2 2 2 2 2 2 A8-B1103 2000 1 4 1 1 1 1 A2-C24 2000 1 1 1 1 1 1

TABLE B2b Post-emergence action: Compound g/ha Panicum Digitaria Echino. Abutilon Xanth. Ipopur. Chenop. A8-Bl 250 4 3 3 3 3 3 2 A2-B1091 250 4 4 2 3 4 3 3 A2-B1094 250 2 3 2 3 3 3 2 A2-B145 250 2 2 2 3 3 3 1 A1208-B354 250 3 4 2 1 2 2 2 A1210-B1 250 2 2 2 2 2 2 1 A8-B552 250 2 3 3 2 2 2 2 A8-B156 250 2 3 3 1 2 2 1 A1210-B1105 250 1 2 3 2 2 2 1 A8-B134 250 3 3 3 2 3 3 2 A8-D36 250 3 3 2 2 3 3 2 A2-D111(cis) 250 2 2 4 2 1 2 2 A2-D111(trans) 250 3 3 3 3 1 3 2 A8-D111 250 3 3 3 3 1 2 3 A8-D109 250 3 3 3 3 1 2 3 A8-F5 250 4 3 4 3 3 3 3 A2-F5 250 3 3 3 3 3 4 3

The same results are obtained when the compounds of the formula I are formulated in accordance with Examples F2 and F4 to F8 in accordance with WO 97/34485. 

What is claimed is:
 1. A compound of the formula I

in which p is 0 or 1; R₅ is C₁-C₆haloalkyl; R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, viny substituted by C₁-C₂alkoxycarbonyl or phenyl, or is C₂-C₆alkynyl, C₂-C₆haloalkynyl, ethynyl which is substituted by trimethylsilyl, hydroxyl, C₁-C₂alkoxy, C₁-C₂alkoxycarbonyl or phenyl, or is C₃-C₆allenyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyl which is substituted by halogen, or is C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-C₁-C₄alkoxy, C₁-C₄alkoxy-C₁-C₄alkoxy, C₁-C₄alkylthio-C₁-C₄alkoxy, C₁-C₄alkylsulfinyl-C₁-C₄alkoxy, C₁-C₄alkylsulfonyl-C₁-C₄alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄-alkoxycarbonyl-7₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, benzyl-S(O)_(n1)—, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylaminosulfonyl, di-(C₁-C₆alkylamino)sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl-containing groups, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro or R₂ is OS(O)_(n2)—R₂₁, N(R₂₃)—S(O)_(n3)—R₂₂, cyano, carbamoyl, C₁-C₄alkoxycarbonyl, formyl, halogen, thiocyanato, amino, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄alkyl, cyano-C₁-C₄alkyl, C₁-C₆alkylcarbonyloxy-C₁-C₄alkyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkyl, C₁-C₄alkoxycarbonyloxy-C₁-C₄alkyl, C₁-C₄thiocyanato-C₁-C₄alkyl, benzoyloxy-C₁-C₄alkyl, C₂-C₆oxiranyl, C₁-C₄alkylamino-C₁-C₄alkyl, di-(C₁-C₄-alkyl)amino-C₁-C₄alkyl, C₁-C₁₂alkylthiocarbonyl-C₁-C₄alkyl or formyl-C₁-C₄alkyl, or R₂ is a five- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C₁-C₄alkylene, —CH═CH—, —C≡C—, —CH₂O—, —CH₂N(C₁-C₄alkyl)—, —CH₂SO—, or —CH₂SO₂ group and it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆alkylaminosulfonyl, C₂-C₆dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or R₃ is —N(R₂₃)—S(O)_(n)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkyl-S(O)_(n)—C₁-C₄alkyl; R₄ is hydrogen, C₁-C₆alkyl, hydroxyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₁-C₄alkylcarbonyloxy, C₁-C₄alkylsulfonyloxy, tosyloxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₁-C₄dialkylamino, C₁-C₄alkoxycarbonyl, C₁-C₄haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or R₄ is a five to ten-membered monocyclic or R₃-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system, unless fused, being bonded to the pyridine ring directly or via a C₁-C₄alkylene, —CH═CH—, —C≡C—, —CH₂O—, —CH₂N(C₁-C₄alkyl)—, —CH₂S—, —CH₂SO—, or —CH₂SO₂— group and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₄alkoxy-C₁-C₂alkylthio, C₁-C₄alkylcarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂alkylthio, cyano-C₁-C₄alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R₂₁ is C₁-C₄alkyl or C₁-C₄haloalkyl; R₂₂ is C₁-C₄alkyl, C₁-C₄haloalkyl or di-(C₁-C₄alkyl)amino; R₂₃, R₂₄, R₂₅ independently of one another are hydrogen or C₁-C₄alkyl; n, n₁, n₂, n₃ and n₄ independently of one another are 0, 1 or 2; Q is Q₁

 in which R₆, R₇, R₈ and R₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkyl-S(O)_(n17), C₁-C₆alkyl-NHS(O)₂, C₁-C₆alkylamino, di-(C₁-C₆alkyl)amino, hydroxyl, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, hydroxy-C₁-C₆alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₆alkyl, tosyloxy-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkyl-S(O)_(n4)—C₁-C₆alkyl, cyano-C₁-C₆alkyl, C₁-C₆alkoxy-C₁-C₆alkoxy, benzyloxy-C₁-C₆alkyl, C₁-C₆alkoxycarbonyl-C₁-C₆alkyl, C₁-C₆alkoxycarbonyloxy-C₁-C₆alkyl, thiocyanato-C₁-C₆alkyl, oxiranyl, C₁-C₆alkylamino-C₁-C₆alkyl, di(C₁-C₆alkyl)amino-C₁-C₆alkyl, formyl-C₁-C₆alkyl, C₁-C₆alkyloximo, halogen, cyano, nitro, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n18), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n5), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n19)N(C₁-C₄alkyl)₂, halogen, nitro, COOH or cyano; or adjacent R₆ and R₇ or R₈ and R₉ together are —(CH₂)_(m)—, C(O)O(CH₂)_(n20)— or —S(O)_(n21)(CH₂)_(n22)—; n₅, n₁₇, n₁₈, n₁₉ and n₂₁ independently of one another are 0, 1 or 2; n₂₀ is 2 or 3; n₂₂ is 2,3 or4; m is 2,3,4,5, or 6; W is oxygen, S(O)_(n6)—CR₁₁R₁₂, —CR₆₃R₆₄CR₆₅R₆₆, —C(O)— or —NR₁₃; R₆₃, R₆₄, R₆₅ and R₆₆ independently of one another are hydrogen or C₁-C₆alkyl, or R₆₅ together with R₇ or R₉ forms a direct bond; n₆ is 0, 1 or 2; R₁₁ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkylthio-C₁-C₄alkyl, C₁-C₄alkylthio-C₃-C₆cycloalkyl, C₁-C₄alkycarbonyloxy-C₁-C₄alkyl, C₁-C₄alkysulfonyloxy-C₁-C₄alkyl, tosyloxy-C₁-C₄alkyl, di-(C₁-C₃alkoxyalkyl)methyl, di-(C₁-C₃alkthioalkyl)methyl, (C₁-C₃alkoxyalkyl)-(C₁-C₃alkthioalkyl)methyl, C₃-C₅oxacycloalkyl, C₃-C₅thiacycloalkyl, C₃-C₄dioxacycloalkyl, C₃-C₄dithiacycloalkyl, C₃-C₄oxathiacycloalkyl, formyl, C₁-C₄alkoxycarbonyl, carbamoyl, C₁-C₄alkylaminocarbonyl, di-(C₁-C₄alkyl)aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n21), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n7), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n20)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; n₇, n₂₀ and n₂₁ independently of one another are 0, 1 or 2; or R₁₂ together with R₆ or R₉ is a group —(CH₂ _(o)—; o is 1, 2, 3, 4 or 5; R₁₂ is hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl; or R₁₂ together with R₁₁ is a group —(CH₂)_(m1); m₁ is 2, 3, 4, 5, or 6; R₁₀ is hydroxyl, O⁻M⁺, halogen, cyano, SCN, OCN, C₁-C₁₂alkoxy, C₁-C₄alkoxycarbonyl-C₁-C₄alkoxy, C₁-C₁₂alkylthio, C₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂haloalkylthio, C₁-C₁₂haloalkylsulfinyl, C₁-C₁₂haloalkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkylthio, C₁-C₆alkoxy-C₁-C₆alkylsulfinyl, C₁-C₆alkoxy-C₁-C₆alkylsulfonyl, C₁-C₁₂alkenylthio, C₂-C₁₂alkenylsulfinyl, C₂-C₁₂alkenylsulfonyl, C₂-C₁₂alkynylthio, C₂-C₁₂alkynylsulfinyl, C₂-C₁₂alkynylsulfonyl, C₂-C₁₂haloalkenylthio, C₂-C₁₂haloalkenylsulfinyl, C₂-C₁₂haloalkenylsulfonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfinyl, C₁-C₄alkoxycarbonyl-C₁-C₄alkylsulfonyl, (C₁-C₄alkoxy)₂P(O)O, C₁-C₄alkyl-(C₁-C₄alkoxy)P(O)O, H(C₁-C₄alkoxy)P(O)O, R₁₄R₁₅N, R₁₄R₁₅NNH, R₁₆R₁₇NC(O)O—, R₁₆R₁₇NC(O)NH—, C₁-C₁₂alkyl-S(O)₂NR₁₈, C₁-C₄haloalkyl-S(O)₂NR₁₉, C₁-C₁ alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)₂O, C₁-C₁₈alkylcarbonyloxy, it being possible for the alkyl group to be substituted by halogen, C₁-C₆alkoxy, C₁-C₆alkylthio or cyano, or is C₂-C₁₈alkenylcarbonyloxy, C₂-C₁₈alkynylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylthiocarbonyloxy, C₁-C₁₂alkylthiocarbamoyl, C₁-C₆alkyl-NH(CS)N(C₁-C₆alkyl)—NH—, di-C₁-C₆alkyl-N(CS)N(C₁-C₆alkyl)—NH—, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano; or R₁₀ is a group Ar₁-thio, Ar₂-sulfinyl, Ar₃-sulfonyl, —OCO—Ar₄ or NH-Ar₅ in which Ar₁, Ar₂, Ar₃, Ar4 and Ar₅ independently of one another are a five to ten-membered monocyclic or fused bicyclic ring system which can be aromatic or partially saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, and it not being possible for each ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄-cyanoalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, di-(C₁-C₂alkyl)aminosulfonyl, di-(C₁-C₄alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic rings are other than halogen; R₁₄, R₁₅, R₁₆, R₁₇ and R₁₈ independently of one another are hydrogen or C₁-C₆alkyl; n₈, n₉, n₁₀, n₁₁, n₁₂, n₁₃ and n₁₄ independently of one another are 0, 1 or 2; R₁₃ is hydrogen, C₁-C₄alkyl, C₁-C₄alkythio-C₁-C₄carbonyl, C₁-C₄alkylsulfinyl-C₁-C₄carbonyl, C₁-C₄alkylsulfonyl-C₁-C₄carbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄alkylcarbonyl, phenylcarbonyl, or is phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄-alkylamino, C₁-C₄alkyl-S(O)_(n15), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n16), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro, or cyano; and n₁₅ and n₁₆ independently of one another are 0, 1 or 2; or an agrochemically tolerated salt M⁺ or a stereoisomer or tautomer of a compound of the formula I.
 2. A compound according to claim 1, wherein p is 0; R₅ is C₁-C₆haloalkyl; R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, benzyl-S(O)_(n1), C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆-alkylaminosulfonyl, C₂-C₆-dialkylaminosulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by C₁-C₃-alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or is OS(O)_(n2)—R₂₁, N(R₂₃)—S(O)_(n3)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkyl-S(O)_(n4)—C₁-C₄alkyl, cyano-C₁-C₄alkyl or C₁-C₄alkoxy-C₁-C₄alkoxy; R₃ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆dialkylamino, C₁-C₆-alkylaminosulfonyl, C₂-C₆-dialkylaminosulfonyl, phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, or is —N(R₂₃)—S(O)_(n)—R₂₂, cyano, halogen, amino, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkyl-S(O)_(n)—C₁-C₄alkyl; R₄ is hydrogen, C₁-C₆alkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyloxy, C₁-C₄-Alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkyl, formyl, cyano, halogen, phenyl or phenoxy, it being possible for phenyl, in turn, to be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or R₄ is a five- to ten-membered monocyclic or R₃-fused bicyclic ring system which can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the ring system being bonded to the pyridine ring via a C₁-C₄alkylene group and it not being possible for the ring system to contain more than 2 oxygen atoms and more than two sulfur atoms, and it being possible for the ring system itself to be mono-, di- or trisubstituted by C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆-Alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₄-alkoxy-C₁-C₂alkylthio, C₁-C₄alkylcarbonyl-C₁-C₂alkylthio, C₁-C₄alkoxycarbonyl-C₁-C₂alkylthio, cyano-C₁-C₄alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, C₂-C₄dialkylaminosulfonyl, halogen, cyano, nitro, phenyl and benzylthio, it being possible for phenyl and benzylthio, in turn, to be substituted on the phenyl ring by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃-haloalkoxy, halogen, cyano or nitro, and where substituents on the nitrogen in the heterocyclic ring are other than halogen; R₂₁ and R₂₂ independently of one another are C₁-C₄alkyl or C₁-C₄haloalkyl; R₂₃ R₂₄ and R₂₅ independently of one another are hydrogen or C₁-C₄alkyl; n, n₁, n₂, n₃ and n₄ independently of one another are 0, 1 or 2; Q is Q₁

 in which R₆, R₇, R₈ and R₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆-haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkyl-S(O)_(n17), C₁-C₆alkyl-NHS(O)₂, C₁-C₆alkylamino, di-(C₁-C₆alkyl)amino, hydroxyl, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆-alkynyloxy, hydroxy-C₁-C₆alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₆alkyl, tosyloxy-C₁-C₆alkyl, halogen, cyano, nitro, phenyl or phenyl which is substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄-alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n18), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n5), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n19)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; or adjacent R₆ and R₇ or R₈ and R₉ together are —(CH₂)_(m)—; n₅ n₁₇, n₁₈ and n₁₉ independently of one another are 0, 1 or 2; m is 2, 3, 4, 5, or 6; W is oxygen, S(O)_(n6), —CR₁₁,R₁₂—, —C(O)— or —NR₁₃—; n₆ is 0, 1 or 2; R₁₁ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy-C₁-C₄alkyl, C₁-C₄alkylthio-C₁-C₄alkyl, C₁-C₄alkylcarbonyloxy-C₁-C₄alkyl, C₁-C₄alkylsulfonyloxy-C₁-C₄alkyl, tosyloxy-C₁-C₄alkyl, di-(C₁-C₃alkoxyalkyl)methyl, di-(C₁-C₃alkylthioalkyl)methyl, (C₁-C₃alkoxyalkyl)-(C₁-C₃alkylthioalkyl)methyl, C₃-C₅oxacycloalkyl, C₃-C₅thiacycloalkyl, C₃-C₄dioxacycloalkyl, C₃-C₄dithiacycloalkyl, C₃-C₄oxathiacycloalkyl, formyl, C₁-C₄alkoxycarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄alkoxycarbonyl, amino, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n21), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n7), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)_(n20)N(C₁-C₄alkyl), halogen, nitro, COOH or cyano; n₇, n₂₀ and n₂₁ independently of one another are 0, 1 or 2; or R₁₂ together with R₉ is a group —(CH₂ _(o)—; o is 1, 2, 3, 4 or 5; R₁₂ is hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl; or R₁₂ together with R₁₁ is a group —(CH₂)_(m1); m₁, is 2, 3, 4, 5, or 6; R₁₀ is hydroxyl, O⁻M⁺, halogen, C₁-C₁₂alkoxy, C₁-C₁₂alkylcarbonyloxy, C₂-C₄-alkenylcarbonyloxy, C₃-C₆cycloalkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂-alkylcarbonyloxy, R₂₃R₂₄N-C(O)O, C₁-C₁₂alkylS(O)_(n8)—, C₁-C₄haloalkyl-S(O)_(n9)—, C₂-C₁₂-alkenylS(O)_(n10)—, C₂-C₁₂haloalkenylS(O)_(n11)—, C₂-C₁₂alkynylS(O)_(n12)—; benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, where the phenyl group, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n13), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n14), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂NH, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano, or is C₁-C₄alkyl-S(O)₂O, phenyl-S(O)₂O, (C₁-C₄-alkoxy)₂P(O)O, C₁-C₄alkyl(C₁-C₄alkoxy)P(O)O, or H(C₁-C₄alkoxy)P(O)O; n₈, n₉, n₁₀, n₁₁, n₁₂, n₁₃ and n₁₄ independently of one another are 0, 1 or 2; R13 is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxycarbonyl or phenyl which, in turn, can be substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkylamino, di-C₁-C₄alkylamino, C₁-C₄alkyl-S(O)_(n15), C₁-C₄alkyl-S(O)₂O, C₁-C₄haloalkyl-S(O)_(n16), C₁-C₄haloalkyl-S(O)₂O, C₁-C₄alkyl-S(O)₂N(C₁-C₄alkyl), halogen, nitro or cyano; n₁₅ and n₁₆ independently of one another are 0, 1 or 2; or an agrochemically tolerated salt M⁺ or a stereoisomer or tautomer of a compound of the formula I.
 3. A compound according to claim 1, in which R₁₀ is hydroxyl or O⁻M⁺.
 4. A compound according to claim 1, in which W is oxygen, —CR₁₁R₁₂— or —C(O)—.
 5. A compound according to claim 1, in which W is oxygen and R₆, R₇, R₈ and R₉ independently of one another are hydrogen or C₁-C₃alkyl.
 6. A compound according to claim 1, in which W is —C(O)— and R₆, R₇, R₈ and R₉ independently of one another are C₁-C₃alkyl.
 7. A compound according to claim 1, in which R₂ is hydrogen and R₃ is methyl.
 8. A compound according to claim 1, in which R₂ is methyl, ethyl, n-propyl, i-propyl, vinyl, methoxymethyl, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl or cyanomethyl.
 9. A compound according to claim 1, in which R₄ is hydrogen or methyl.
 10. A compound according to claim 1, in which R₅ is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl or difluoromethyl.
 11. A compound according to claim 1, in which R₃ is hydrogen and R₂ is C₁-C₄alkyl, C₁-C₃haloalkyl, cyclopropyl, C₂-C₃alkenyl, C₂-C₃haloalkenyl, C₂-C₃alkynyl, allenyl, C₁-C₂-alkoxy-C₁-C₂alkyl, C₁-C₂alkylthio-C₁-C₂alkyl, cyano-C₁-C₂alkyl, C₁-C₂alkoxycarbonyl-C₁-C₂-alkyl, C₁-C₄alkylcarbonyloxy-C₁-C₂alkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, allyloxy, propargyloxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl or cyano.
 12. A herbicidal and plant-growth-inhibitory composition, which has a herbicidally active content of a compound of the formula I according to claim 1 and an inert carrier.
 13. A method of controlling undesired vegetation, in which a herbicidally active amount of an active ingredient of the formula I according to claim 1 or of a composition comprising said active ingredient is applied to the plants or to their environment.
 14. A method of inhibiting plant growth, in which a herbicidally active amount of an active ingredient of the formula I according to claim 1 or of a composition comprising said active ingredient is applied to the plants or to their environment. 